Photoinduced coupling of acetylenes and quinone in the solid state as preorganized donor-acceptor pairs

被引：19

作者：

Bosch, E ^{[1
]}

Hubig, SM ^{[1
]}

Lindeman, SV ^{[1
]}

Kochi, JK ^{[1
]}

机构：

[1] Univ Houston, Dept Chem, Houston, TX 77204 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 03期

关键词：

D O I：

10.1021/jo971470n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Crystalline electron donor-acceptor (EDA) complexes of various diarylacetylenes (DA) and dichlorobenzoquinone (DB) are isolated and structurally characterized by X-ray crystallography. Deliberate excitation of either the DB acceptor at lambda(DB) = 355 nm or the 1:2 [DA, 2DB] complex at lambda(CT) = 532 nm in the solid state leads to [2 + 2] cycloaddition and identical (isomeric) mixtures of the quinone methide products. Time-resolved (ps) diffuse reflectance spectroscopy identifies the ion-radical pair [DA(.+), DB.-] as the reactive intermediate derived by photoinduced electron transfer in both photochemical procedures. The effects of crystal-lattice control on the subsequent ion-radical pair dynamics are discussed in comparison with the same photocouplings of acetylenes and quinone previously carried out in solution.

引用

页码：592 / 601

页数：10

共 44 条

[31] MOLECULAR COMPOUNDS AND THEIR SPECTRA .3. THE INTERACTION OF ELECTRON DONORS AND ACCEPTORS [J].