Exciplex Ensemble Modulated by Excitation Mode in Intramolecular Charge-Transfer Dyad: Effects of Temperature, Solvent Polarity, and Wavelength on Photochemistry and Photophysics of Tethered Naphthalene-Dicyanoethene System

被引:7
作者
Aoki, Yoshiaki [1 ]
Matsuki, Nobuo [1 ]
Mori, Tadashi [1 ]
Ikeda, Hiroshi [2 ]
Inoue, Yoshihisa [1 ]
机构
[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] Osaka Prefecture Univ, Grad Sch Engn, Dept Appl Chem, Naka Ku, Sakai, Osaka 5998531, Japan
关键词
CHIRAL FUMARATE; DYNAMICS; PHOTOCYCLOADDITION; STEREOSELECTIVITY; ALKENES;
D O I
10.1021/ol502394g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Solvent, temperature, and excitation wavelength significantly affected the photochemical outcomes of a naphthalene-dicyanoethene system tethered by different number (n) of methylene groups (1-3). The effect of irradiation wavelength was almost negligible for 2a but pronounced for 3a. The temperature dependence and theoretical calculations indicated the diversity of exciplex conformations, an ensemble of which can be effectively altered by changing excitation wavelength to eventually switch the regioselectivity of photoreactions.
引用
收藏
页码:4888 / 4891
页数:4
相关论文
共 33 条
[1]   PHOTOCHEMICAL CYCLOADDITIONS OF BENZONITRILE TO ALKENES - FACTORS CONTROLLING SITE OF ADDITION [J].
CANTRELL, TS .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (26) :4238-4245
[2]   DIVERGENT PATHWAYS IN PHOTOCHEMICAL REACTIONS OF BENZONITRILE [J].
CANTRELL, TS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (16) :5929-&
[3]   RETENTION OF CONFIGURATION AT MIGRATING CENTRE IN BOTH PHOTOCHEMICAL AND THERMAL [1,3]-SIGMATROPIC SHIFT OF A BENZYL GROUP - RELAXATION OF ORBITAL SYMMETRY CONTROL IN AN UNSYMMETRICAL ALLYL SYSTEM [J].
COOKSON, RC ;
KEMP, JE .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (08) :385-&
[4]   THE WAVELENGTH-DEPENDENT AND SOLVENT-DEPENDENT PHOTOCHEMISTRY OF 1,1-DICYANO-2-METHYL-4-PHENYLBUT-1-ENE - REACTION FROM 2 EXCITED-STATES [J].
COOKSON, RC ;
SADLER, DE ;
SALISBURY, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (05) :774-782
[5]   Model studies of spectral and photophysical characteristics of a series of donor-acceptor-polyenes of different length [J].
El-Gezawy, Hani ;
Rettig, Wolfgang .
CHEMICAL PHYSICS, 2006, 327 (2-3) :385-394
[6]   Some applications of the transition state method to the calculation of reaction velocities, especially in solution. [J].
Evans, MG ;
Polanyi, M .
TRANSACTIONS OF THE FARADAY SOCIETY, 1935, 31 (01) :0875-0893
[7]   The activated complex in chemical reactions [J].
Eyring, H .
JOURNAL OF CHEMICAL PHYSICS, 1935, 3 (02) :107-115
[8]  
Ferreira A. B. B., 1978, J CHEM SOC P2, V2, P995
[9]   NATURE OF ELECTROPHILES AND ELECTRON-ACCEPTORS - COMPARISON OF THEIR MOLECULAR-COMPLEXES WITH AROMATIC DONORS [J].
FUKUZUMI, S ;
KOCHI, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (21) :4116-4126
[10]   Intramolecular charge transfer in 4-aminobenzonitriles does not necessarily need the twist [J].
Gómez, I ;
Reguero, M ;
Boggio-Pasqua, M ;
Robb, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :7119-7129