Radical cations from diarylamino-substituted fluorenones

被引：4

作者：

Homnick, Paul J. ^{[1
]}

Tinkham, Jonathan S. ^{[1
]}

Lahti, Paul M. ^{[1
]}

机构：

[1] Univ Massachusetts, Dept Chem, Amherst, MA 01003 USA

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 01期

关键词：

Aminium cations; Radical cations; Triarylamines; NIR absorbing materials; Intervalence charge transfer; Hush model; Intramolecular electron transfer; ENERGY-LEVELS; TRIARYLAMINE; TRIPHENYLAMINE; GENERATION; POLYMERS;

D O I：

10.1016/j.tetlet.2012.10.060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chemical oxidation of diarylamino-substituted fluorenones gives highly persistent radical cations, some of which can be stored in the solid state for months. Solution UV-vis-NIR spectra show strong monoradical cation absorption bands in the 750-1700 nm range, with minimum energy about 0.73 eV. 2,7-Bis(dianisylamino)fluorenone exhibits strong absorptions at 1670 (monocation) and 873 nm (dication). Fast intervalence electron transfer behavior between amine sites in the monocation is indicated by EPR spectroscopic and absorption spectral Hush analyses. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：35 / 39

页数：5

共 50 条

[21] Theoretical studies on the dimerization of substituted paraphenylenediamine radical cations
Punyain, Kraiwan
Kelterer, Anne-Marie
Grampp, Guenter
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2011, 83 (01) : 368 - 378
[22] Substituent effects in pericyclic reactions of radical cations: The ring opening of 3-substituted cyclobutene radical cations
Swinarski, DJ
Wiest, O
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20): : 6708 - 6714
[23] Triplet excited states and radical intermediates formed in electron pulse radiolysis of amino-substituted fluorenones
Samant, V
Singh, AK
Mukherjee, T
Palit, DK
RADIATION PHYSICS AND CHEMISTRY, 2005, 72 (06) : 711 - 722
[24] ISOMERIZATION OF METHOXY-SUBSTITUTED AND CARBOMETHOXY-SUBSTITUTED CYCLOALKYL-RADICAL AND ALKENE-RADICAL CATIONS
SCHWARZ, H
WESDEMIOTIS, C
LEVSEN, K
HEIMBACH, H
WAGNER, W
ORGANIC MASS SPECTROMETRY, 1979, 14 (05): : 244 - 253
[25] A GENERAL-SYNTHESIS OF SUBSTITUTED FLUORENONES AND AZAFLUORENONES
KYBA, EP
LIU, ST
CHOCKALINGAM, K
REDDY, BR
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15): : 3513 - 3521
[26] Theoretical study of highly substituted butadiene radical cations.
Oxgaard, J
Wiest, O
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U157 - U158
[27] HOMOCONJUGATION IN RADICAL CATIONS OF 7-SUBSTITUTED QUADRICYCLANES AND NORBORNADIENES
ROTH, HD
DU, XM
WENG, HX
LAKKARAJU, PS
ABELT, CJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) : 7744 - 7752
[28] VIBRONIC SPECTRA OF RADICAL CATIONS OF SOME HYDROXYL SUBSTITUTED NAPHTHALENES
SHARMA, AK
ZAIDI, ZH
MACHWE, MK
INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 1994, 33 (02): : 145 - 147
[29] Synthesis and properties of a (diarylamino)ferrocene and its radical cation
Mendiratta, A
Barlow, S
Day, MW
Marder, SR
ORGANOMETALLICS, 1999, 18 (03) : 454 - 456
[30] DISSOCIATIVE IONIZATION OF METHYL-SUBSTITUTED FLUORENES AND FLUORENONES
SHEVTSOV, VK
ZVOLINSKII, VP
ZAKHAROV, PI
PLESHAKOV, VG
ALEKSEEVA, LA
PROSTAKOV, NS
ZHURNAL ORGANICHESKOI KHIMII, 1982, 18 (11): : 2415 - 2421

← 1 2 3 4 5 →