Toroidal hopping of a single hole through the circularly-arrayed naphthyl groups in hexanaphthylbenzene cation radical

被引:36
作者
Chebny, Vincent J. [1 ]
Shukla, Ruchi [1 ]
Rathore, Rajendra [1 ]
机构
[1] Univ Wisconsin, Dept Chem, Milwaukee, WI 53201 USA
关键词
D O I
10.1021/jp063654o
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Synthesis of a dendritic ( soluble) hexanaphthylbenzene derivative is described in which the six naphthyl groups are connected to the central benzene ring in a propeller-shaped arrangement. Observation of multiple oxidation waves in its cyclic voltammogram as well as an intense charge-resonance transition ( extending beyond 1600 nm) in its cation radical, generated by laser-flash photolysis using photoexcited chloranil as an oxidant, suggests that a single hole is mobilized via electron transfer ( or hopping) over six identical ( circularly arrayed) redox centers.
引用
收藏
页码:13003 / 13006
页数:4
相关论文
共 35 条
[1]   FORMATION OF DIMER CATIONS OF AROMATIC HYDROCARBONS [J].
BADGER, B ;
BROCKLEH.B .
NATURE, 1968, 219 (5151) :263-&
[2]   ABSORPTION SPECTRA OF DIMER CATIONS .1. OLEFINS [J].
BADGER, B ;
BROCKLEH.B .
TRANSACTIONS OF THE FARADAY SOCIETY, 1969, 65 (562P) :2576-&
[3]   INTRAMOLECULAR EXCIMER FORMATION AND FLUORESCENCE QUENCHING IN DINAPHTHYLALKANES [J].
CHANDROSS, EA ;
DEMPSTER, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (12) :3586-+
[4]  
FRITZ HP, 1978, ANGEW CHEM, V90, P305
[5]   Intramolecular dimer radical cations of α,ω-di(2-naphthyl)alkanes in solutions studied by near-IR transient absorption spectroscopy [J].
Fushimi, T ;
Fujita, Y ;
Ohkita, H ;
Ito, S .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2004, 165 (1-3) :69-74
[6]   RESTRICTED ROTATION IN HEXAARYLBENZENES [J].
GUST, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (21) :6980-6982
[7]   DYNAMIC STEREOCHEMISTRY OF HEXAARYLBENZENES [J].
GUST, D ;
PATTON, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (26) :8175-8181
[8]   Steric control of electron transfer. Changeover from outer-sphere to inner-sphere mechanisms in arene/quinone redox pairs [J].
Hubig, SM ;
Rathore, R ;
Kochi, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :617-626
[9]   TIME-RESOLVED OBSERVATION OF EXCITATION HOPPING BETWEEN 2 IDENTICAL CHROMOPHORES ATTACHED TO BOTH ENDS OF ALKANES [J].
IKEDA, T ;
LEE, B ;
KURIHARA, S ;
TAZUKE, S ;
ITO, S ;
YAMAMOTO, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) :8299-8304
[10]   Hexaterphenylyl- and hexaquaterphenylylbenzene: The behavior of chromophores and electrophores in a restricted space [J].
Keegstra, MA ;
DeFeyter, S ;
DeSchryver, FC ;
Mullen, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (07) :774-776