Modulating the Photochemistry of Bipyridylic Compounds by Symmetric Substitutions

被引:4
作者
Ortiz-Sanchez, Juan M. [1 ]
Gelabert, Ricard [1 ]
Moreno, Miquel [1 ]
Lluch, Jose M. [1 ]
机构
[1] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Cerdanyola Vall, Spain
关键词
conical intersections; substituent effects; excited states; photochemistry; proton transfer; INTRAMOLECULAR-PROTON-TRANSFER; DENSITY-FUNCTIONAL THEORY; TRANSFER EXCITED-STATES; CHARGE-TRANSFER; AB-INITIO; TRANSIENT ABSORPTION; ELECTRONIC-STRUCTURE; DYNAMICS; STABILIZATION; SPECTROSCOPY;
D O I
10.1002/cphc.201000596
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
A quantum electronic study of the effect of substituents on (2,2'-bipyridyl)-3,3'-diol and (2,2'-bipyridyl)-3,3'-diamine is presented. A large difference in the photochemical behavior between the original and the substituted selected systems is expected. For the sake of simplicity, the study is restricted to the symmetrically bi-substituted compounds: fluorine, the more electronegative atom and thus a strong sigma-acceptor but also a weak pi-donor group, and NO2, a strong pi-acceptor substituent. Among the large set of compounds studied, two receive special attention: 5,5'-dinitro-(2,2'-bipyridyl)-3,3'-diamine and 6,6'-difluoro-(2,2'-bipyridyl)-3,3'-diol. While in the former case the nitro substitution transforms (2,2'-bipyridyl)-3,3'-diamine, previously suggested to behave as a photomemory material, into a simple fluorescent species, the latter substitution turns (2,2'-bipyridyl)-3,3'-diol into a fresh new candidate for a photomemory device.
引用
收藏
页码:3696 / 3703
页数:8
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