Generation and Spectroscopic Profiles of Stable Multiarylaminium Radical Cations Bridged by Fluorenes

被引:32
作者
Chang, Chao-Che [1 ]
Yueh, Han [1 ]
Chen, Chao-Tsen [1 ]
机构
[1] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
关键词
PALLADIUM-CATALYZED SYNTHESIS; DELOCALIZATION; SYSTEMS; ROUTE;
D O I
10.1021/ol2007988
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of arylaminofluorene derivatives (DTFA-1, TTFA-2, TAFB-3, and TAFA-4) were synthesized, and the generation of their corresponding arylaminium cation radicals was readily achieved by Cu(ClO4)(2) in CH3CN. Moreover, the cation radicals were stable at ambient temperature with substantially long life times and exhibited distinct colors. The oxidation mechanism and spectroscopic features of the resulting cation radicals were probed by UV-vis-NIR spectroscopy and electron spin resonance experiments.
引用
收藏
页码:2702 / 2705
页数:4
相关论文
共 29 条
[1]   Intervalence transitions in the mixed-valence monocations of bis(triarylamines) linked with vinylene and phenylene-vinylene bridges [J].
Barlow, S ;
Risko, C ;
Chung, SJ ;
Tucker, NM ;
Coropceanu, V ;
Jones, SC ;
Levi, Z ;
Brédas, JL ;
Marder, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (48) :16900-16911
[2]   Achieving high-efficiency non-doped blue organic light-emitting diodes: charge-balance control of bipolar blue fluorescent materials with reduced hole-mobility [J].
Chi, Chih-Chin ;
Chiang, Chih-Long ;
Liu, Shun-Wei ;
Yueh, Han ;
Chen, Chin-Ti ;
Chen, Chao-Tsen .
JOURNAL OF MATERIALS CHEMISTRY, 2009, 19 (31) :5561-5571
[3]   Chemical redox agents for organometallic chemistry [J].
Connelly, NG ;
Geiger, WE .
CHEMICAL REVIEWS, 1996, 96 (02) :877-910
[4]   Electronic couplings in organic mixed-valence compounds:: The contribution of photoelectron spectroscopy [J].
Coropceanu, V ;
Gruhn, NE ;
Barlow, S ;
Lambert, C ;
Durivage, JC ;
Bill, TG ;
Nöll, G ;
Marder, SR ;
Brédas, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (09) :2727-2731
[5]  
Davies AG, 2001, J CHEM RES, P253
[6]   Room-temperature high-spin organic single molecule: Nanometer-sized and hyperbranched poly[1,2,(4)-phenylenevinyleneanisylaminium] [J].
Fukuzaki, E ;
Nishide, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (03) :996-1001
[7]   Generation and conversions of aromatic amine radical cations in acid zeolites [J].
García, H ;
Martí, V ;
Casades, I ;
Fornés, V ;
Roth, HD .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2001, 3 (14) :2955-2960
[8]  
GURAM AS, 1995, ANGEW CHEM INT EDIT, V34, P1348, DOI 10.1002/anie.199513481
[9]   Polycationic States of Oligoanilines Based on Wurster's Blue [J].
Ito, Akihiro ;
Sakamaki, Daisuke ;
Ino, Haruhiro ;
Taniguchi, Aya ;
Hirao, Yasukazu ;
Tanaka, Kazuyoshi ;
Kanemoto, Katsuichi ;
Kato, Tatsuhisa .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (26) :4441-4450
[10]   Delocalization in platinum-alkynyl systems:: A metal-bridged organic mixed-valence compound [J].
Jones, SC ;
Coropceanu, V ;
Barlow, S ;
Kinnibrugh, T ;
Timofeeva, T ;
Brédas, JL ;
Marder, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) :11782-11783