イオン化エネルギー 固体物性研究の観点から関心がもたれると思われる有機化合物を中心として、実験によって決められた孤立分子とその固体のイオン化エネルギーの値を集めた。 データの収集にあたっては、最近までの報告値をなるべく多く検討し、その結果として分子と固体についてそれぞれ次のような値の収録を行った。ただし、既に以前に報告値が収束しているような化合物も少なくなく、そのような場合には古い値をそのまま掲載したものもある。なお、たとえば次の文献を参照されたい。 K. Seki, メIonization energies of free molecules and molecular solids,モ Mol. Cryst. Liq. Cryst. 171 (1989) 255. (1) 孤立分子については、典型的な電子供与体と電子受容体を含む多くの芳香族化合物を対象として、気相の第一イオン化エネルギー(Ig)を集めた。同一化合物に対し複数の値が報告されている場合には、紫外光電子分光法(UPS)により決定された最も信頼性が高いと思われる値を一つだけ示すことを原則とした。 分子とその正イオンとの間に起こる電子の脱離/付加過程を考えると、分子のイオン化エネルギーの値には断熱値(adiabatic ionization energy, Ia)、垂直脱離値(vertical detachment ionization energy, Idv)、垂直付加値(vertical attachment ionization energy, Iav)の三種類がある。そして、しばしばこれらの間には Idv > Ia > Iav の関係が認められる。今回収集したデータは UPS による決定値であり、この方法では多くの場合スペクトルの第一ピークの値から Idv が求まる。しかし、そのピーク形状から Ia が見積れる場合もあるため、原報に測定スペクトルが示されている場合にはそれも検討した。このようにして Ia が求められた化合物もあり、そのような値についてはそれと分かるようにした。 (2) 固体のイオン化エネルギー(Is)としては、高分子のデータを別にしてイオン化閾値が報告されている物質のほぼ総てについて、その値を集めた。なお、それらの値には、UPS で決められたものと、光電子放出の量子収量の励起光エネルギー依存性(PQY)やその他の方法で決められたものとがある。 孤立分子と固体のイオン化エネルギーの双方が報告されている物質については、分子の気相から固相への凝集に基づく緩和エネルギーも示した。この緩和エネルギーは、両相のイオン化エネルギーの差 D = Ig ミ Is として定義される量である。この量がもつ意味などについては、たとえば次の文献を参照されたい。 N. Sato, メMolecular electronic relaxation in organic solids,モ Electrical and related properties of organic solids, R. W. Munn, A. Miniewicz and B Kuchta (eds.), (Kluwer Academic Publishers, Dordrecht, 1997), pp. 157 - 166. 【化合物別の収録順序(イオン化エネルギー)】 RARE GASES AND SIMPLE INORGANIC COMPOUNDS SIMPLE ORGANIC COMPOUNDS POLYCYCLIC AROMATIC HYDROCARBONS METHYL- AND PHENYL-SUBSTITUTED AROMATIC HYDROCARBONS OTHER SUBSTITUTED HYDROCARBONS HETEROCYCLES AMINES QUINONES ELECTRON ACCEPTORS PHTHALOCYANINES AND PORPHYRINS METALLOCENES LONG ALKYL COMPOUNDS DIACETYLENE COMPOUNDS DYES AND PIGMENTS Alizaline Dyes Azine Dyes Azo Dyes Carotenoids Cyanines Furanquinone Pigments Indene Derivatives Merocyanines Oxazine Dyes Thiazine Dyes Triphenylmethane Dyes Viologen Dyes Xanthene Dyes Others MOLECULAR COMPLEXES Organic-Organic Complexes Inorganic-Organic Complexes NOTE REFERENCES Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ RARE GASES AND SIMPLE INORGANIC COMPOUNDS Neon 21.56 SKJ85 20.3 SKJ85 1.3 Argon 15.76 SKJ85 13.9 SKJ85 1.9 Krypton 14.00 SKJ85 11.9 SKJ85 2.1 Xenon 12.13 SKJ85 9.7 SKJ85 2.4 Nitrogen 15.57 TBBB70 14.0 HSK75 1.5 14.2 LFK82 Oxygen 12.07 TBBB70 10.5 HSK75 1.6 Iodine 9.26* KKAYI81 6.34 YSI87 2.92 H2O 12.61 TBBB70 9.9 YMS75 2.7 9.85 Su CO2 13.78 TBBB70 12.3 HSK75 1.5 11.9 FLK84 NH3 10.16 TBBB70 8.3 YMS75 1.9? SF6 15.5 KMJBS76 14.3 FK85 1.2 SIMPLE ORGANIC COMPOUNDS Methane 12.70 TBBB70 11.2 HSK75 1.2 Neopentane 10.2* JSGC72/3 8.7 SI83 1.5 Hexane 10.25* Hp 8.55 SI83 1.7 3-Methylpentane 10.2* Hp 8.85 SI83 1.4 2,2-Dimethylbutane 10.2* Hp 8.8 SI83 1.4 Cyclohexane 9.88 BHHM77 8.2 SI83 1.7 Methylcyclohexane 9.5 BHHM77 8.3 SI83 1.2 Ethylene 10.51 B79a 9.1 ? 1.4 1-Hexene 9.37 AB78 7.6 SI78 1.8 Acetylene 11.40 TBBB70 9.7 FK84 1.7 Methanol 10.8* KKKAYI81 8.7 YMS75 2.1 Ethanol 10.3* KKKAYI81 8.3 YMS75 2.0 Formaldehyde 10.9* TBBB70 8.4 YMS75 2.5 CH2Cl2 11.2* KKAIY81 9.4 YSIu 1.8 CHCl3 11.3* KKAIY81 9.3 YSIu 2.0 CCl4 11.4* KKAIY81 9.4 YSIu 2.0 9.4 FK85 CBr4 10.2 GGJOT70 7.3 SI87 2.9 CI4 9.00 JDS82 5.50 SI87 3.50 C2Br4 9.105 PNL83 6.17 SI87 2.9 C2I4 8.57 JVMDS82 5.04 SI87 3.5 Tetramethylsilane 9.79 JSGS72/3 8.2 SI83 1.6Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ POLYCYCLIC AROMATIC HYDROCARBONS Benzene 9.17 CBH72 7.3 YMS75 2.1 7.1 Su 7.58 AS75 Naphthalene 8.12* CBH72 6.4 SSI81 1.7 8.15 BMS72 6.84 LM62 6.76ト LM60 Anthracene 7.36* CBH72 5.67ト SSI83a 1.7 7.47 BCS74 5.75 KSSI82 5.70 SSI81 5.88 NES74 5.7 5.75 HHI77 5.65 VS72 5.65ト LM60 5.85 HVK68 5.65 5.68 KHHI70 5.5 V13 5.6-6.2 H12 (4.9-5.6) VZG63 5.85 MK70 5.95ト MK70 5.75 FHI72 Naphthacene 6.89* CBH72 5.10 SSI81 1.8 7.04 BCS74 5.25 VZG63 5.40 5.43 KHHI70 5.26ト LM60 5.38 KC61 5.3 HVK68 5.24 HI66 5.31 BL68 5.2 ZV71 5.3 SHKI76 5.4ィ APH79 Pentacene 6.58* CBH72 4.85 Ht 1.7 6.74 BMS72 5.1 VZG63 5.06 5.04 KHHI70 5.08 KC61 4.95 SHKI76 5.07 HI66 Hexacene 6.43 BCS74 Phenanthrene 7.86 BMS72 6.08ト SISK85 1.8 6.13 SISK85 6.45ト LM60 Chrysene 7.51 BMS72 5.8 SSI81 1.7 5.73ト LM60 Benz[a]anthracene 7.38 BMS72 5.64 Ht 1.7 7.41 BCS74 5.68ト LM60 5.76 ZV71 Benzo[c]phenanthrene 7.6 BH72 6.2 SSI81 1.4 7.60 S77 Triphenylene 7.81 BS72 6.2 H2t 1.6 7.89 BCS74 Napth[2,1-a]anthracene 7.2 SSI81 5.45 H2t 1.8 7.14 BCS74 Dibenz[a,h]anthracene 7.35 SSI81 5.55 H2t 1.8 7.38 BCS74 5.69ト LM60 Picene 7.5 BMS72 5.7 H2t 1.8 7.54 BCS74 Dibenzo[g,p]chrysene 6.97* BCS74 5.8 SSI81 1.2 Pyrene 7.37 BS72 5.58ト SISK85 1.7 7.41 BCS74 5.83 SISK85 5.8 Ht 5.84 5.85 HHI74 5.81ト LM60 5.78ィ GR69 Benzo[a]pyrene 7.12 BMS72 5.4 BL68 1.7 Dibenzo[fg,op]naphthacene 7.26* SSI81 5.7 SSI81 1.6 7.40 BCS74 Perylene 6.90* SSI81 5.12ト SSI83 1.8 7.00 BCS74 5.2 SHKI76 5.40 5.33 KHHI70 5.40 BL68 5.39 KC61 5.40 KHI67 5.2 SHKI76 5.26ィ GR69 5.65 ABM76 Benzo[ghi]perylene 7.12* BMS72 5.26ト SISK85 1.9 7.19 BCS74 5.44 SISK85 5.4 SSI81 Coronene 7.25* BS72 5.52 Ht 1.7 7.36 BCS74 5.59 5.58 HKAIH69 5.3 SHKI76 5.15 BL68 Pyranthrene 5.05 5.04 HKAIH69 Violanthrene A 6.42 SSI81 4.86 SSI81 1.6 5.20 5.06 HKAIH69 4.96 HI66 5.20 KC61 5.0 ABS74 Isoviolanthrene A 6.36 SISAI82 4.92 SISAI82 1.4 ?5.20 HKAIH69 5.0 ABS74 Violanthrene B 6.36 SISAI82 4.82 SISAI82 1.5 5.13 HKAIH69 Isoviolanthrene B 6.54 SISAI82 4.96 SISAI82 1.6 Tetrabenzo[a,cd,j,lm]perylene 6.58 SISAI82 5.34 SISAI82 1.2 Tetrabenzo[de,hi,op,st]pentacene 6.13 SISAI82 4.98 SISAI82 1.2 Quaterrylene 6.11 CS78 4.76 HI66 1.4 Ovalene 6.86 BMS72 Hexabenzo[a,d,g,j,m,p]coronene 6.87 SC78 Graphite 4.7 WFF71 Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ Biphenyl 8.2 E72 p-Terphenyl 7.9 HSI75 6.1 5.8 HSI75 1.8 7.8 SKEKS84 6.2 SHKI76 Sexiphenyl 7.2 SKEKS84 5.9 SKEKS84 1.3 Bibenzyl 8.75* PMRL71 7.2 Su 1.6 Acenaphthene 7.82 BCS74 Acenaphtylene 8.22 BCS74 Biphenylene 7.53 E72 Fluoranthene 7.95 BCS74 Decacyclene 5.40 KC61 4.74 IKH67 Azulene 7.43 BCS74 Benz[a]indeno[1,2,3-cd]azulene 6.84 SSI81 5.0 SSI81 1.9 ________________________________________________________________________________ Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ METHYL- AND PHENYL-SUBSTITUTED AROMATIC HYDROCARBONS Toluene 8.67 DR72/3 7.28 AS75 1.4 o-Xylene 8.4* K72 m-Xylene 8.5* K72 p-Xylene 8.3* K72 Hexamethylbenzene 7.85^ VT57 1-Methylnaphthalene 7.95v HHPT72 2-Methylnaphthalene 7.93v HHPT72 9-Methylanthracene 7.23 HI74 5.75 5.68 HHI77 1.5 5.56 VS72 2,3-Dimethylanthracene 5.41ト SISK85 9,10-Dimethylanthracene 5.43 VS72 9-Phenylanthracene 9.0* SSBV72 6.10 MK70 2.9? 9,10-Diphenylanthracene 7.05 BCS74 5.85 SSI81 1.2 6.25ト MK70 6.05 MK70 5.85 FHI73 9,9'-Bianthryl 7.2 HHI77 5.9 5.96 HHI77 1.3 Rubrene 6.41 THSSIF79 5.3 THSSIF79 1.1 5.10 BL68 Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ OTHER SUBSTITUTED AROMATIC HYDROCARBONS Phenol 8.48 E69 Fluorobenzene 8.9* BMT68 Chlorobenzene 8.9* BMT68 Bromobenzene 9.0* BMT68 Iodobenzene 8.4* BMT68 Methoxybenzene 8.0* BMT68 Benzonitrile 9.2* BMT68 Nitrobenzene 9.6* BMT68 p-Dinitrobenzene 10.3 EGR75 Hexachlorobenzene 8.98 SSI81a 7.3 SSI81a 1.7 Hexabromobenzene 8.80 SSSI81a 7.1 SSSI81a 1.7 Hexaiodobenzene 7.90 SSSI81a 5.9 SSSI81a 2.0 9-Bromoanthracene 6.10 MK70 9,10-Dichloroanthracene 7.5* SW74 5.8 5.75 HHI77 1.7 6.10 MK70 9,10-Dibromoanthracene 7.5* SW74 6.08 MK70 1.4 1,6-Dicyanopyrene 6.33 6.23 HHI74 1,3,6,8-Tetrachloropyrene (6.26) HHI74 1,3,6,8-Tetrabromopyrene 5.97 HHI74 1,3,6,8-Tetracyanopyrene 6.21 6.35 HHI74 1,3,6,8-Tetranitropyrene 6.56 6.52 HHI74 HETEROCYCLICS Thiophene 8.87 E69 Pyrrole 8.209 DAEL71 Pyridine 9.26 TBBB70 7.3 YMS75 2.0 (8.0) FSK84 1.3 Pyrazine 9.28 E69 Indole 7.75* E69 Quinoline 8.5* VV72 Isoquinoline 8.4* VV72 Carbazole 7.53 HCH75 5.87 KSSI82 1.5 7.60 RKKG78 6.66 NES74 Acridine 7.88 HCH75 ca.6.2 MK70 1.7? 8.13 MMKY75 Phenazine 8.4 MMKY75 ca.7.1 MK70 1.3? Phenothiazine 6.82 HH75 5.15ト SISK85 1.5 6.72 DMH77 5.18 SISK58 5.18 KSSI82 4.99 KC61 ca.4.8 Mt Dibenzophenothiazine 5.21 5.36 HKAIH69? Benzo[b]naphtho[2,3-d]furan (Brazan) 5.77ト SISK85 5.81 Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ Promazine ca.5.1 Mt Promazine hydrochloride ca.5.4 Mt Chloropromazine ca.4.7 Mt Chloropromazine hydrochloride ca.5.2 Mt Adenine 8.0* PPL76 7.0 PI76 1.0 6.4 SBRPS73 Guanine 7.85 DYVAM78 Cytosine 8.45 DYVAM78 7.5 PI76 1.0 Tymine 8.95 DWMM76 7.7 PI76 1.3 Uracil 9.34 DWMM76 7.8 PI76 1.5 Tryptophan 7.3 SI79 6.1 Su 1.2 Reserpine 5.2 Mt Tetraphenyl[3,4-c]thienothiophene 6.1 MSCL76 6a-Thiathiophthene 8.11 GHLHL71 5.88 SKu 2.1 2,5-Dimethyl-6a-thiathiophthene 7.59 GHLHL71? 5.73 SKu 1.9 2,5-Dimethyl-6a-thia-1-azapentalene 7.00 GHLHL71? 5.61 SKu 1.4 NMe,NMe,H,H? (5.25) SKu 1,2,5,6-Tetramethyl-6a-thia-1,6- 6.3* GGR75 4.93 SKu 1.4 diazapentalene 1,8-Dithianaphthalene 7.0* SCNEH78 5.75 SCNEH78 1.3 Tetrathianaphthacene (TTN) 6.07 SIS81 4.4 SIS81 1.7 4.55 4.42 KHHI70 4.56 HI66 4.53 KHI67 4.56 IKH67 4.75 4.75 BA71 Tetraselenanaphthacene 4.45 SKIH76 Tetrathiafulvalene (TTF) 6.4 GSCF73 5.0 NES74 1.4 6.4 BCW74 DimethylTTF (DMTTF) 6.00 SIS81 5.1 SIS81 0.9 TetramethylTTF (TMTTF) 6.03 SIS81 4.9 SIS81 1.1 HexamethyleneTTF (HMTTF) 6.06 SSI83 4.63 SSI83 1.4 TetrathiomethoxyTTF (TTMTTF) 6.29 SSI83 5.00 SSI83 1.3 Bis(ethylenedithiolo)TTF 6.21 SSI83 4.78 SSI83 1.4 (BEDT-TTF) DibenzoTTF (DBTTF) 6.68 SIS81 4.4 SIS81 2.3 Tetraselenafulvalene (TSF) 6.68 STE77 4.99 SSI83 1.7 TetramethylTSF (TMTSF) 6.27 GKSFBBC79 4.84 SSI83 1.4 HexamethyleneTSF (HMTSF) 6.12 SSI83 4.75 SSI83 1.4 Hexamethylnenetetratellurafulvalene 6.81 SSIp 4.87 SSIp 2.9 (HMTTeF) Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ AMINES Methylamine 8.95 TWI85 Ethylamine 8.78 TWI85 n-Butylamine 8.59 TWI85 Dimethylamine 8.18 TWI85 Diethylamine 7.99 TWI85 Trimethylamine 7.79 TWI85 Triethylamine 7.37 TWI85 Tri(n-propyl)amine 7.18 TWI85 Tetrakis(dimethylamino)ethylene 5.36 CKKLP71 (TDAE) Aniline 7.71 E69 N-Methylaniline 7.4* TBBB70 5.9 Su 1.5 N,N'-Dimethylaniline 7.1 EGR75 o-Phenylenediamine 7.2 TST73 m-Phenylenediamine 7.44 TST73 p-Phenylenediamine (PD) 6.84 TST73 5.2 HVK68 1.7 N,N,N',N'-Tetramethyl-p- 6.2 EGR75 5.0 Su 1.2 phenylenediamine (TMPD) 4.63 BL68 4.7 HVK68 1-Naphthylamine 7.1* M74 2-Naphthylamine 7.5* M74 1,5-Naphthalenediamine 6.74 M74 1,8-Naphthalenediamine 6.65 M74 1,6-Pyrenediamine 4.71 BL68 Diphenylamine 7.18 DR74 Triphenylamine 6.82 SY92 5.42 SY92 1.4 6.75 DR74 Diphenyl-p-tolylamine 6.78 SY92 5.59 SY92 1.2 Phenyldi(p-tolyl)amine 6.52 SY92 5.52 SY92 1.0 Tri(p-tolyl)amine 6.48 SY92 5.42 SY92 1.1 Benzidine (BD) 5.10 BL68 N,N,N',N'-TetramethylBD 5.26 BL68 N,N-Diethyl-N'-(2,4-dinitrobenzo)- 5.5 ZV71 p-phenylenediamine (AK-4) 5.55 5.55 ABB70 Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ QUINONES p-Benzoquinone 9.95 DW69 p-Chloranil (CA) 9.74 SSI81a 8.1 SSI81a 1.6 5.0? HVK68 p-Bromanil (BA) 9.59 SSI81a 7.4 SSI81a 2.2 5.0? HVK81a p-Iodanil (IA) 8.58 SSI81a 5.6 SSI81a 3.0 Dichlorodicyano-p-benzoquinone 5.68 5.64 HKAIH69 (DDQ) Anthraquinone 9.05 LSS75 7.6 NSAFI88 1.5 Pyranthrone 5.83 5.71 HKAIH69 Violanthrone 5.10 KHHI70 5.32 KLu Indanthrone 5.10 KHI67 5.17 KHHI70 5.26 KLu ELECTRON ACCEPTORS Pyromellitic dianhydride (PMDA) 10.9* GCD79 8.0 ISSSI76 2.9 Tetracyanoethylene (TCNE) 11.7 ISFIOK74 Tetracyano-p-quinodimethane 9.5 ISFIOK74 7.4 St 2.1 (TCNQ) 7.88 NES74 Tetracyanonaphthoquinodimethane 8.5 ISSKKI 6.0 ISSKKI 2.5 (TNAP) SSITH79 AAITH79 Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ PHTHALOCYANINES AND PORPHYRINS Metal-free-phthalocyanine( PC) 6.1* B79 5.15 VZG63 0.95 5.12 BL68 5.15 KC61 5.20ィ P62 5.05-5.22 KLu 、6.0(error)! VT60 5.0 St1 Al-PC 5.0 VZG63 Ca-PC 5.00 KLu Cu-PC 6.1* B79 (a-form) 4.88 CSISQ83 1.2 (b-form) 4.62 CSISQ83 1.5 5.0 VZG63 5.0ィ P62 Chlorinated Cu-PC 6.0 St1 Fe-PC 6.1* B79 4.85 VZG63 1.25 4.95 KC61 5.00ィ P62 Pb-PC 6.1* B79 5.00 KLu 1.1 Mg-PC 6.1* B79 4.75 VZG63 1.35 4.96ィ P62 4.85ィ P62a 4.70 BBFA72 4.80 BBFA72 Ni-PC 6.2* B79 4.8 St1 1.4 4.95 KC61 Na-PC 5.1 St1 4.94 KLu Zn-PC 6.1* B79 6.0(error)! VT60 5.2 St1 0.9? Co-PC 6.1* B79 Protoporphyrin 4.9 St1 1.2? Tetraphenylporphyrine (TPP) 6.39v KR75 Zn-TPP 6.2 KR75 5.0 SKIY80 1.2 Mg-TPP 6.3 KR75 4.85 BA71a 1.5? Ethioporphyrin 5.29 KC61 Hemin 5.3 SKIY80 Chlorophyll a (4.8) VZG63 Chlorophyll b 5.25 NFI79 Cytochrome c (oxidized) 6.1 KSHYI78 (reduced) 5.8 KSHIY78 Cytochrome c3 (oxidized) 5.4 KSHYI78 (reduced) 4.6 SKIY80 Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ METALLOCENES Ferrocene 6.72 RWBKHS72 5.4 RNM77 1.3 5.75 MK70 Ruthenocene 6.15 MK70 Nickellocene 6.2 RWBKHS72 Decamethylferrocene 5.7 CGKPTRS80 4.7 RNM77 1.0 Decamethylnickellocene 4.4 CGKPTRS80 LONG ALKYL COMPOUNDS Hexatriacontane 9.1 SHSH11K77 Stearic acid (on In2O3: crystalline) 7.8 MTSSI85 (on Cu) 8.1 MTSSI85 (on Au: amorphous) 8.4 MTSSI85 Perfluoroundecanoic acid 8.5 MSI88 1,4-Bis-stearylaminoanthraquinone 6.0 NFSAI87 Tetrakis(ethylthia)TTF 5.15 STMWSI86 5.00 YSIS87 Tetrakis(propylthia)TTF 4.94 Yu Tetrakis(butylthia)TTF 4.83 Yu Tetrakis(pentylthia)TTF 4.86 Yu Tetrakis(hexylthia)TTF 4.83 Yu Tetrakis(hepthylthia)TTF 4.89 Yu Tetrakis(octylthia)TTF 4.80 STMWSI86 Tetrakis(nonylthia)TTF 4.65 STMWSI86 Tetrakis(decylthia)TTF 4.70 STMWSI86 4.65 Yu 4.60 YSIS87 Tetrakis(undecylthia)TTF 4.64 Yu Tetrakis(dodecylthia)TTF 4.67 Yu Tetrakis(tridecylthia)TTF 4.63 Yu Tetrakis(tetradecylthia)TTF 4.7 STMWSI86 Tetrakis(pentadecylthia)TTF 4.71 Yu Tetrakis(hexadecylthia)TTF 4.74 Yu Tetrakis(heptadecylthia)TTF 4.69 Yu Tetrakis(octadecylthia)TTF 4.85 STMWSI86 DIACETYLENE COMPOUNDS 2,4-Hexadiyne-1,6-bis(p-toluene sulfonate) 6.9ィ A82 7.1 MSB82 Tricosa-10,12-diynoic acid 6.7 NFSAI87 DYES AND PIGMENTS #: Compound cannot be identified definitely. #1: Probably. #2: Probably 3-allyl-3'-ethyl-5',6'-dimethyl-4-keto-5-[2-(4(1H)-dihydroauinolinylidene)- ethylidene]-thiazolinooxacyanine bromide. #3: The figure in the original paper corresponds to 3-amino-2-p-methoxyphenylindene-1-one. #4: Probably 1-oxo-3-oxido-2-pyridinioindene is a better structure reflecting the properties of this. #5: The structural formula in the original paper corresponds to 3-phenylamino-2-phenylindenone-1. #6: Probably victoria pure blue BO. Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ Alizaline Dyes Alizarin blue 7.35 V60 5.4 KV61 1.9 Azine Dyes Phenosafranine 5.4 KV61 Azo Dyes Bismarck brown 5.5 Mt Carotenoids b-Carotene 6.5 DYVAM78 5.5、 VT60 1.0 Cyanines Cyanine# 5.28 F30 Kryptocyanine 5.0 ABVT67 4.2-3 N61 Pinacyanol 7.25ニ 4.9 VT60a 2.35 Pinacyanol (chloride) 4.6 N61 Pinakryptol yellow 5.4 KAB71 Quinoline blue#1 7.35 V60 4.5 KV61 2.85 (ethylcyanine) 3,3'-Diethylthiacyanine bromide 5.5 TYIISOTu perchlorate 5.4 TYIISOTu tosylate (p-toluene sulfonate) 5.65 TYIISOTu 3,3'-Diethylthiacarbocyanine 5.0 N61 bromide 5.15 TYIISOTu perchlorate 5.05 TYIISOTu tosylate 5.27 TYIISOTu 3,3'-Diethylthiadicarbocyanine bromide 4.9 TYIISOTu perchlorate 4.9 TYIISOTu tosylate 5.1 TYIISOTu Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ 3,3'-Diethylthiatricarbocyanine bromide 4.7 TYIISOTu perchlorate 4.73 TYIISOTu tosylate 5.0 TYIISOTu 3,3'-Diethylenthiapentacarbocyanine 5.1 ABVT67 iodide 3-Allyl-3'-ethyl-5,6'-dimethyl-4-keto-5-(1-dihydro- 4.8 KV61 quinolidene-4-ethylidene)thiazalinooxacyanine bromide#2 3,3'-Dimethyl-9,11,15,17-bis(b,b'-dimethyltri- 5.2 ABVT67 methylene)thiapentacarbocyanine iodide 1,1'-Dimethyl-10-phenyl-2,2'-carbocyanine bromide 4.6 N61 Furanquinone Pigments 8,13-dioxodinaphto[2,1-b:2',3'-d]furan- (on Al) 6.45 PN72 6-(2-pyridyl)carboxamide (on ox. Al) 6.3 PN72 Indene Derivatives 3-Amino-2-methoxyphenylindone-1#3 5.25 BA69 5.50 GST73 2-Pyridino-1,3-indanedione (betaine)#4 5.75 NSS77 3-Phenylamino-2-phenylindone-1#5 5.35 BA69 5.50 GST73 1-Phenylamino-2-phenylindene-i-thione-3 5.25 BA69 5.25 GST73 trans-Bis-bindodiene# 4.80 BA69 4.85 4.85 ABB71 Merocyanines Merocyanine# 7.35 V60 5.6 KV61 1.75 3-Ethyl-5-(3-ethylbenzothiazolin-2-ylidene)rhodanine 5.55 TSIT86 3-Ethyl-5-[2-(3-ethylbenzothiazolin2-ylidene)- 5.10 TSIT86 ethylidene]rhodanine 3-Ethyl-5-[4-(3-ethylbenzothiazolin2-ylidene)-2- 4.85 TSIT86 butenylidene]rhodanine 3-Ethyl-5-[6-(3-ethylbenzothiazolin2-ylidene)-2,4- 4.75 TSIT86 hexadienylidene]rhodanine 3-Ethyl-5-{4-[3-(3-sulfopropyl)benzothiazolin-2- 4.80 TSIT86 ylidene]-2-butenylidene}rhodanine 3-Ethyl-5-[2-(3-ethylthiazolidin-2-ylidene)ethyl- 5.20 TSIT86 indene]rhodanine 3-Carboxymethyl-5-[2-(3-ethylthiazolidin-2- 5.20 TSIT86 ylidene)ylideneethylidene]rhodanine 5-[2-(1,3-Diethyl-5-chlorobenzimidazolin-2- 5.15 TSIT86 ethylidene]-3-hexylrhodanine 5-[2-(1,3-Diethyl-5-nitrobenzimidazolin-2- 5.20 TSIT86 ylidene)ethylidene]-3-hexylrhodanine Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ Oxazine Dyes Nile blue A 5.17 Mt Triphenodioxazine (TPDO) 4.94 SSNFKI86 DichloroTPDO 5.75 SSNFKI86 Thiazine Dyes Methylene blue 5.4 KV61 5.2 Mt Triphenodithiazine(TPDT) 5.12 SSNFKI86 DichloroTPDT 5.61 SSNFKI86 TetrachloroTPDT 5.2 Mt Triphenylmethane Dyes Aurin 5.4、 VZG63 Crystal Violet 5.0 KV61 3.45 Mt 5.00 KLu (Br-) 5.0 N61 (Cl-) 5.1 N61 (acetate) 5.2 N61 Malachite green 5.2 KV61 (Cl-) 5.2 N61 (oxalate) ca.5.2 N61 Night blue 4.7 Mt Victoria pure blue 30#6 5.00 Mt Fuchsin 4.15 F30 Basic fuchsin (Cl) 5.6% N61 Viologen Dyes Methyl viologen (reduced) 3.6 MKI76 (oxidized) 4.8 4.8-9 MKI76 Xanthene Dyes Erythrosine 5.5 VT60 Erythrosine (Na) 5.5% N61 Rhodamin B 5.10ィ GR69 5.1 KV61 Rhodamin 6G 7.26 V60 5.7 VT60 1.6 Others Indigo red# 7.32 V60 5.0 KV61 1.3 Indigo blue 7.17 V60 5.4 KV61 1.7 Golden-orange indanthrene# (5.3-5.8) VZG63 Pinakryptol# 5.2、 VT60a Yellow indanthrene# (5.2-5.6) VZG63 MOLECULAR COMPLEXES DDQ: Dichlorodicyano-p-benzoquinone PMDA: Pyromellitic dianhydride TCNQ: Tetracyanoquinodimethane TMPD: N,N,N',N'-Tetramethyl-p-phenylenediamine TNB: 1,3,5-Trinitrobenzene Compound Ig/eV Ref. Is/eV Ref. D/eV UPS PQY etc. ________________________________________________________________________________ Organic-Organic Complexes (Anthracene)(TNB) (5.88) BL68 (Anthracene)(TCNQ) 6.17 NES74 5.03 BL68 (Anthracene)(PMDA) 6.00 KSSI82 6.0 ISSSI76 5.26 BL68 (Pyrene)(TNB) 5.60 BL68 (Pyrene)(TCNQ) 5.70 BL68 (1,2-Benzanthracene)(TCNQ) 5.00 BL68 (Chrysene)(TNB) (5.50) BL68 (Coronene)(Trinitrobenzene) 5.62 HKAIH69 (Perylene)(TNB) (5.54) BL68 (Perylene)(Dicyanomethylenetrinitrofluorene) 5.23 BL68 (Perylene)(p-Chloranil) 5.40 BL68 (Perylene)(o-Chloranil) 5.35 BL68 (Perylene)(TCNQ) (5.50) BL68 (Perylene)(PMDA) 5.16 BL68 (Violanthrene)(o-Chloranil) 5.32 KC61 (Carbazole)(TCNQ) 6.76 NES74 (Carbazole)(PMDA) 6.22 KSSI82 (Acridine)(PMDA) 6.3 KSSI82 (Phenothiazine)(o-Chloranil) 5.38 KC61 (Phenothiazine)(PMDA) 5.41 KSSI82 (N-Methylphenazinium)(TCNQ) 6.0 NES74 (Bibenzophenothiazine)(DDQ) 4.99 HKAIH69 (Bibenzophenothiazine)2(DDQ) 4.75 HKAIH69 (Tetrathianaphthacene)(TCNQ)2 4.75 AAB77 (Tetrathiafulvalene)(TCNQ) (5.07)タ NES74 (5.6)タ GPEMS74 (p-Phenylenediamine)(Chloranil) 5.4 HVK68 (p-Phenylenediamine)(Bromanil) 5.4 HVK68 (TMPD)(p-Chloranil) 5.0 HVK68 4.88 BL68 (TMPD)(p-Bromanil) 4.85 HVK68 4.87 BL68 (TMPD)(TCNQ) (from p-xylene) 4.86 BL68 (from glacial acetic acid) 4.72 BL68 (1,6-Diaminopyrene)(o-Chloranil) 4.88 BL68 (1,6-Diaminopyrene)(p-Chloranil) 4.39 BL68 (1,6-Diaminopyrene)(p-Bromanil) (4.65) BL68 (1,6-Diaminopyrene)(TCNQ) 4.58 BL68 (Benzidine)(TCNQ) 5.03 BL68 (N,N,N',N'-Tetramethylbenzidine)(TNB) 4.72 BL68 (H2-Phthalocyanine)(o-Chloranil) 5.29 KC61 (Fe-Phthalocyanine)(o-Chloranil) 5.32 KC61 (Decamethylferrocene)(TCNQ)2 4.7 RNM77 (Quinolinium)(TCNQ)2 5.35 NES74 4.85 HKAIH69 Inorganic-Organic Complexes Li(TCNQ) 5.6 NES74 Na(Anthracene) 3 MKu Na(o-Chloranil) 5.50 Mt Na(TCNQ) 5.6 NES74 K(o-Chloranil) 5.35 Mt K(TCNQ) 5.8 GPEMS74 Rb(Benzonitrile) 5.01 KTI70 5.05 KI72 Rb(Benzonitrile) (+H2) 4.90 KTI70 Cs(Pyrene) 1.5 OIIH65 Cs(Perylene) 2.2 YSIu Cs(Triphenylene) 2.40 KI72 Cs2(Triphenylene) 2.43 KI72 Cs(Violanthrene) 1.54 IH63 2.95 ABS74 Cs(Tetranitropyrene) 1.8 OIIH65 Cs(Tetrachloropyrene) 1.8 OIIH65 Cs(Tetrabromopyrene) 1.8 OIIH65 Cs(Tetracyanopyrene) 1.3 OIIH65 Cs2(TCNQ)3 3.0 LSS75a NH4(TCNQ) 4.9 SKSI75 NOTES Gas phase *: Value read from the reported spectrum. v: Vertical ionization energy. ^: Value determined from photoionization experiment. Solid state : Raw value determined from photoemission quantum yield measurements. (Those authors also reported values corrected for estimated surface/bulk difference effects). ( ): Values claimed to be dubious by the authors. ?: Dubious values. ト: Value for a single crystal. ィ: Millikan method. !: Stated to be erroneous in VZG63. ニ: Cast doubt on the possibility of decomposition by Nelson [N67]. 、: Photoelectron spectrum is rather featureless. %: Resolution is reduced to 0.4 eV due to low light intensity. タ: Cast doubt on the possibility of different surface composition from the bulk [LSS75, NSE75]. REFERENCES [A82] S. Arnold, J. Chem. Phys. 76 (1982) 3842. [AAB77] V. V. Aleksandrov, S. B. Aleksandrov and D. R. Balode, Dokl. Akad. Nauk SSSR 234 (1977) 825. [AB75] V. V. Aleksandrov and A. I. Belkind, Izv. Akad. Nauk Latv. SSR, Ser. Fiz. Tekh. Nauk (1975) No. 5, 53. [AB78] F. S. Ashmore and A. R. Burgess, J. Chem. Soc. Faraday Trans. 2 74 (1978) 734. [ABB70] S. B. Aleksandrov, D. R. 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Inokuchi, J. Chem. Phys. 86 (1987) 1755. [YSIu] H. Yamamoto, K. Seki and H. Inokuchi, unpublished results. [Yu] H. Yamamoto, unpublished results. [ZV71] A. A. Zagrubskii and F. I. Vilesov, Fiz. Tverd. Tela 13 (1971) 1927: Sov. Phys. Solid State 13 (1972) 1927. 電子親和力 固体物性研究の観点から関心がもたれると思われる有機化合物を中心として、実験によって決められた孤立分子の電子親和力の値を集めた。 データの収集にあたっては、十年ほど前に相次いで総説(たとえば、後に掲げる文献のうち DMB84, KC87, JB87, LBLHLM88, CW89 など)が出版されて以来、この方面の研究がクラスターを含むイオンやラジカルなどに向かったため、実質的にはあまりデータが増えていないことを踏まえて、それらの総説中に取り上げられた物質とその値を主に選んだ。 ただし、近年、アメリカの National Institute of Standards and Technology (NIST) が種々のデータべースを構築している中に S. G. Lias らが編集している電子親和力のデータベースも存在するので、その最新(1998 年 11 月)版の内容もチェックしたうえで必要に応じてデータを NIST98 からの引用として加えた。 いうまでもなく、電子親和力の実験的な決定方法は次頁に示すように一通りではない。そのため、方法の違いによって得られる値には偏差が認められる場合がある。また、同じ方法を用いたとしても測定装置に依存する誤差要素が異なりうる。これらの結果として、同一物質に対する報告値が広い範囲にわたってばらつく場合も少なくない。そこで、今回収集したデータにはなるべくその決定方法や誤差を記すこととし、また、複数の値が報告されている場合には、一応の評価を行って selected value を示すことにした。ただし、このような作業は実は膨大な労力を要するものであるため、決して十分に行えたとはいえない状況にある。なお、上述の NIST のデータベースについては、収録されている値の出典が明示されていないため、その評価は必ずしも容易ではないことを付記しておく。 分子とその負イオンとの間に起こる電子の付着/脱着過程を考えると、分子の電子親和力の値には断熱値(adiabatic electron affinity, Aa)、垂直脱着値(vertical detachment electron affinity, Adv)、垂直付着値(vertical attachment electron affinity, Aav)の三種類がある。そして、しばしばこれらの間には Adv > Aa > Aav の関係が認められる。今回収集したデータがこれらのどれに当たるかを本来は明確に示すべきだが、それには値のそれぞれについて少なくとも原報を調べる必要があり、そこまでは手が回らなかった。ただし、どの電子親和力に当たるのか示したものが一部にはあり、また測定方法の判明している値については、次頁に記す方法の特徴から求まる値の素性が分かるものもある。【電子親和力の測定方法】 略号 方法名 → 主に求まる値 《参考文献》 (英語名称) CD (or CI) 衝突脱離(イオン化)法 → Adv 《JB79》 (Collisional detachment; Collisional ionization technique) CT (or ECT) (吸熱)電荷移動法 → Adv 《JB79》 (Charge transfer; Endothermic charge-transfer) CTS 電荷移動吸収分光法[溶液法] → Av 《CW75》 (Charge-transfer spectroscopic method in solution) EC (or ECD) 電子捕獲法 → Aa 《CW89》 (Electron capture; Electron capture detector technique) ET 電子透過(分光)法 → Aa 《JB87》 (Electron transmission) ETE 電子移動平衡法 → Aa 《KC87》 (Electron transfer equilibrium) HWRP 半波還元電位[溶液法]→ Aa 《CW89》 (Half-wave reduction potential method in solution) LPES レーザー光電子分光法 → Adv 《HL85》 (Laser photoelectron spectroscopy) LPT (or LPD) レーザー光脱離閾値法 → Adv 《HL85》 (Laser photodetachment threshold; Laser photodetachment technique) MT (or M) マグネトロン法 → Aa 《CW89》 (Magnetron method) PT 光脱離閾値法 → Adv 《HL85》 (Photodetachment threshold) 【化合物別の収録順序(電子親和力)】 SIMPLE INORGANIC COMPOUNDS Diatomic molecules Triatomic molecules Polyatomic molecules SIMPLE ORGANIC COMPOUNDS Methane derivatives Benzophenone derivatives Alkene derivatives Alkyne derivatives AROMATIC HYDROCARBONS AND THEIR DERIVATIVES Benzene derivatives Naphthalene derivatives Anthracene derivatives Others QUINONES AND THEIR DERIVATIVES Benzoquinone derivatives Naphthoquinone derivatives Anthraquinone derivatives NONBENZENOID COMPOUNDS HETEROCYCLIC COMPOUNDS REFERENCES Compound Ag/eV Method Ref. Comment ________________________________________________________________________________ SIMPLE INORGANIC COMPOUNDS Diatomic molecules O2 0.440(8) LPES DMB84 S2 1.670(15) LPES DMB84 Se2 1.96(5) LPT SCMFB89 Te2 1.92(7) LPES DMB84 NO 0.024(10) LPES DMB84 F2 3.08(10) CT DMB84 Cl2 2.38(10) CT DMB84 Br2 2.55(10) CT DMB84 I2 2.55(5) CT DMB84 IBr 2.55(10) CT DMB84 Triatomic molecules CS2 0.895(20) LPES OE NO2 2.275(25) LPT DMB84 selected value 2.30 ETE KC87 N2O イ1.465 CT DMB84 O3 2.1028(25) LPT DMB84 SO2 1.097(36) LPES CBH74 1.107(8) LPES NE selected value S2O 1.877(8) LEPS NE SeO2 1.83(5) LPES SCMFB89 Polyatomic molecules Fe(CO)2 1.22(2) LPES DMB84 Fe(CO)3 1.8(2) LPES DMB84 HNO3 0.57(15) CD DMB84 Ni(CO)2 0.643(14) LPES DMB84 Ni(CO)3 1.077(13) LPES DMB84 SF6 0.5 - 0.8 CD CW89 1.05(10) ETE GCK85 1.15(15) EC CW89 1.10(10) CW89 selected value 1.4(4) MT CW89 PCl3 0.82(10) CD DMB84 PBr3 1.59(15) CD DMB84 SO3 ウ1.70(15) CD DMB84 C60 2.6-2.8 YPCCS87 2.650(50) LPD WCJS91 C72 3.300 NIST98 C78 3.010 NIST98 C80 3.700 NIST98 C84 3.050 NIST98 Compound Ag/eV Method Ref. Comment ________________________________________________________________________________ SIMPLE ORGANIC COMPOUNDS Methane derivatives CH3CN ミ2.84 LBLHLM88 CH3I 0.2(1) CT DMB84 CH3NO2 0.44(20) CD DMB84 0.45(10) EC CW89 selected value 0.48(10) ETE KC87 CH2Cl2 1.31(5) MT CW89 CHCl3 1.70(5) MT CW89 selected value 1.76 LBLHLM88 CCl4 2.0(2) CT CW89 2.06(10) MT CW89 selected value 2.08(20) CT CW89 Benzophenone derivatives Benzophenone 0.64(5) EC CW89 selected value 0.65(10) CT CW89 4-Fluorobenzophenone 0.64(5) EC CW89 0.65(5) CW89 selected value 0.66(10) CT CW89 4-Bromobenzophenone 0.90 CW89 4-Chlorobenzophenone 0.8(1) EC CW89 0.84(10) CT CW89 selected value 4-Iodobenzophenone 1.00 CW89 4-Methoxybenzophenone 0.64 CW89 Perfluorobenzophenone 1.61 LBLHLM88 Alkene derivatives Ethylene ミ1.3 JB87 adiabatic value ミ1.74 JB87 vertical value Trichloroethylene 0.400 NIST98 1,1-Diphenylethylene 0.390 NIST98 Maleic anhydride 1.4(2) CD DMB84 1.42(10) CW89 selected value 1.44(10) CT CW89 trans-Dicyanoethylene 0.78(10) MT CW89 1.0(2) CW89 1.24(10) ETE KC87 selected value Tetracyanoethylene 2.3(3) PT DMB84 2.88(5) MT FP67 2.90(10) CTS CW89 selected value 3.17(10) ETE CK86 trans-2-Butene ミ2.10 LBLHLM88 Butadiene ミ0.62 ET JB87 Hexacyanobutadiene 3.24(7) MT CW89 Cyclohexene ミ2.13 ET JB87 Cyclooctatetraene 0.60 CW89 1,3-Cyclopentadiene ミ1.05 LBLHLM88 Alkyne derivatives Acetylene ミ2.6 ET JB78 Compound Ag/eV Method Ref. Comment _______________________________________________________________________________ AROMATIC HYDROCARBONS AND THEIR DERIVATIVES Benzene derivatives Benzene 0.72 EC CW89 adiabatic value ミ1.15 ET CW89 vertical value tert-Butylbenzene ミ1.06 LBLHLM88 Bromobenzene ミ0.70 LBLHLM88 Chlorobenzene ミ0.75 LBLHLM88 o-Dichlorobenzene 0.09 CW89 p-Dichlorobenzene 0.18 CW89 Pentachlorobenzene 0.729 NIST98 Hexachlorobenzene 0.915 NIST98 o-Dicyanobenzene 0.95(10) CT CW89 1.0(1) CW89 selected value 1.04(10) MT CW89 p-Dicyanobenzene 1.10 CW89 Fluorobenzene ミ0.89 LBLHLM88 1,2,3,5-Tetramethylbenzene 0.108 NIST98 1,2,4,5-Tetramethylbenzene 0.048 NIST98 Pentamethylbenzene 0.182 NIST98 Hexamethylbenzene 0.121 NIST98 Nitrobenzene >0.7(2) CT DMB84 >0.8(2) EC CW83 1.01(10) CT CW89 selected value o-Dinitrobenzene 1.65 CW89 m-Dinitrobenzene 1.62 CW89 p-Dinitrobenzene 1.96 CW89 o-Bromonitrobenzene 1.17 CW89 m-Bromonitrobenzene 1.32 CW89 p-Bromonitrobenzene 1.29 CW89 o-Chloronitrobenzene 1.12 CW89 m-Chloronitrobenzene 1.28 CW89 p-Chloronitrobenzene 1.26 CW89 m-Cyanonitrobenzene 1.53 CW89 p-Cyanonitrobenzene 1.72 CW89 m-Fluoronitrobenzene 1.22 CW89 p-Fluoronitrobenzene 1.11 CW89 m-Methoxynitrobenzene 1.04 CW89 p-Methoxynitrobenzene 0.91 CW89 m-(Trifluoromethyl)nitrobenzene 1.41 CW89 2,3-Dimethylnitrobenzene 0.81 CW89 2,6-Dimethylnitrobenzene 0.71 CW89 3,4-Dimethylnitrobenzene 0.89 CW89 1,3,5-Trichlorobenzene 0.34 CW89 1,2,4,5-Tetrachlorobenzene 0.45 CW89 1,2,4,5-Tetracyanobenzene 2.15(22) MT CW89 1,4-Dicyanotetrafluorobenzene 1.89 CW89 Pentafluorobenzene 0.434 NIST98 Hexacyanobenzene 2.48(13) MT CW89 Hexafluorobenzene 0.52(10) CT CGHK86 0.86(3) EC CW89 selected value 1.20(8) MT CW89 Compound Ag/eV Method Ref. Comment ________________________________________________________________________________ (Trifluoromethyl)benzene 0.002 NIST98 Acetophenone 0.34 CW89 p-Cyanoacetophenone 1.13 LBLHLM88 o-Nitroacetophenone 1.38 LBLHLM88 m-Nitroacetophenone 1.31 LBLHLM88 p-Nitroacetophenone 1.55 LBLHLM88 Aniline ミ1.13 LBLHLM88 m-Nitroaniline 0.95 LBLHLM88 N,N-Dimethyl-3-nitroaniline 0.95 CW89 Anisole ミ1.09 LBLHLM88 Benzaldehyde 0.41 CW89 m-Phthalaldehyde 0.971 NIST98 m-Cyanobenzaldehyde 1.00 LBLHLM88 p-Cyanobenzaldehyde 1.22 LBLHLM88 o-Nitrobenzaldehyde 1.51 LBLHLM88 m-Nitrobenzaldehyde 1.41 LBLHLM88 p-Nitrobenzaldehyde 1.67 LBLHLM88 Benzonitrile 0.24 CW89 o-Nitrobenzonitrile 1.61 LBLHLM88 m-Nitrobenzonitrile 1.56 LBLHLM88 p-Nitrobenzonitrile 1.72 LBLHLM88 2,6-Dinitrobenzonitrile 0.72 LBLHLM88 3,5-Dinitrobenzonitrile 2.16 LBLHLM88 Pentafluorobenzonitrile 0.94 LBLHLM88 Toluene ミ1.11 LBLHLM88 o-Nitrotoluene 0.92 CW89 m-Nitrotoluene 0.8(2) EC CW89 0.99(10) CT CW89 selected value p-Nitrotoluene 0.95 CW89 Octafluorotoluene >1.7(3) CT DMB84 Phenol ミ1.01 LBLHLM88 o-Xylene ミ1.12 LBLHLM88 m-Xylene ミ1.06 LBLHLM88 p-Xylene ミ1.07 LBLHLM88 Biphenyl ミ0.3 LBLHLM88 o-Nitrobiphenyl 1.07 CW89 p-Nitrobiphenyl 1.20 CW89 Perfluorobiphenyl 0.91 LBLHLM88 Phthalic anhydride 1.21 CW89 Compound Ag/eV Method Ref. Comment ________________________________________________________________________________ Naphthalene derivatives Naphthalene 0.15 CW89 1-Chloronaphthalene 0.28 CW89 1-Ethylnaphthalene 0.147 NIST98 2-Ethylnaphthalene 0.195 NIST98 1-Methylnaphthalene 0.160 NIST98 2-Methylnaphthalene 0.143 NIST98 1-Naphthalenecarbonitrile 0.6765 NIST98 1-Naphthalenecarboxaldehyde 0.681 NIST98 2,3-Dimethylnaphthalene 0.173 NIST98 2,6-Dimethylnaphthalene 0.160 NIST98 1-Naphthaldehyde 0.68(3) EC CW89 0.69(3) CW89 selected value 0.70(10) CT CW89 2-Naphthaldehyde 0.62(3) EC CW89 0.63(3) CW89 selected value 0.65(10) CT CW89 1-Nitronaphthalene 1.23 CW89 2-Nitronaphthalene 1.18 CW89 1,3-Dinitronaphthalene 1.78 LBLHLM88 1,5-Dinitronaphthalene 1.77 LBLHLM88 Anthracene derivatives Anthracene 0.56(5) EC CW89 0.57(5) CW89 selected value 0.60(10) CT CW89 1-Chloroanthracene 0.78 CW89 2-Chloroanthracene 0.75 CW89 9-Chloroanthracene 0.86 LBLHLM88 9-Cyanoanthracene 1.27 LBLHLM88 9-Nitroanthracene 1.43 LBLHLM88 Compound Ag/eV Method Ref. Comment ________________________________________________________________________________ Others Phenanthrene 0.31 CW89 Naphthacene 0.88 CW89 Chrysene 0.41 CW89 Triphenylene 0.29 CW89 Benz[a]anthracene 0.64 CW89 Benzo[c]phenanthrene 0.54 CW89 Pyrene 0.56 CW89 Dibenz[a,h]anthracene 0.64 CW89 Dibenz[a,j]anthracene 0.64 CW89 Pentacene 1.392 NIST98 Perylene 0.350 NIST98 Benzo[a]pyrene 0.67 CW89 Benzo[e]pyrene 0.534 NIST98 Picene 0.542 NIST98 Benzo[ghi]perylene 0.420 NIST98 Coronene 0.540 NIST98 Indene 0.173 NIST98 Biphenylene 0.890 NIST98 Fluorene 0.278 NIST98 Acenaphthylene 0.403 NIST98 Fluoranthene 0.63 CW89 QUINONES AND THEIR DERIVATIVES Benzoquinone derivatives o-Benzoquinone 1.620 NIST98 p-Benzoquinone 1.34(9) MT CW89 1.89(30) CD DMB84 1.91(10) CT CW89 selected value 1.92(10) CT CW89 Methyl-p-benzoquinone 1.85 CW89 Phenyl-p-benzoquinone 2.04 CW89 tert-Butyl-p-benzoquinone 1.88 CW89 2,6-Di(tert-butyl)-p-benzoquinone 1.88 CW89 2,5-Dichloro-p-benzoquinone 2.41 CW89 2,6-Dichloro-p-benzoquinone 2.48 CW89 2,5-Dimethyl-p-benzoquinone 1.77 CW89 Trimethyl-p-benzoquinone 1.63 CW89 Tetrafluoro-p-benzoquinone 2.27 MT CW89 2.45(10) CT CW89 2.6(1) CW89 selected value 2.70(10) CT CW89 2.92(20) CD DMB84 Tetrachloro-o-benzoquinone 2.440 NIST98 Tetrachloro-p-benzoquinone 2.40(26) MT CW89 2.7(1) CW89 selected value 2.76(20) CD DMB84 2.77(10) CT CW89 2.78(10) CT CW89 Tetrabromo-p-benzoquinone 2.44(20) CD DMB84 Compound Ag/eV Method Ref. Comment ________________________________________________________________________________ Tetracyano-p-quinodimethane 2.80(10) MT CW89 2.80(10) CD CW89 2.80(3) CD CW89 2.8(3) CD DMB84 2.82(10) CW89 selected value 2.83(18) MT CW89 Tetrafluorotetracyano-p-quinodimethane 3.38(10) CW89 Naphthoquinone derivatives 1,4-Naphthoquinone 1.81 CW89 2,3-Naphthoquinone 2.19 LBLHLM88 2-Methyl-1,4-naphthoquinone 1.74 CW89 Anthraquinone derivatives 9,10-Anthraquinone 1.15(10) MT CW89 1.59 CW89 selected value 2-tert-Butyl-9,10-anthraquinone 1.56 ETE HCSK88 2-Ethyl-9,10-anthraquinone 1.56 ETE HCSK88 NONBENZENOID COMPOUNDS Azulene 0.69(5) EC CW89 selected value 0.69(10) CT CW89 HETEROCYCLIC COMPOUNDS Pyrrole ミ2.38 LBLHLM88 Furan ミ1.76 LBLHLM88 Thiophene ミ1.17 LBLHLM88 Pyridine ミ0.62 LBLHLM88 2,3,5,6-Tetracyanopyridine 1.59(10) CT CW89 2.12(17) MT CW89 selected value 2.17 CW89 Pentafluoropyridine 0.681 NIST98 Pyridazine 0.250 NIST98 Pyrazine 0.400 NIST98 1,3,5-Triazine 0.450 NIST98 Acridine 0.906 NIST98 Phenazine 1.305 NIST98 REFERENCES [CBH74] R. 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