4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes modified for extended conjugation and restricted bond rotations

被引:270
作者
Chen, J [1 ]
Burghart, A [1 ]
Derecskei-Kovacs, A [1 ]
Burgess, K [1 ]
机构
[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA
关键词
D O I
10.1021/jo991927o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Five new, constrained, aryl-substituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes (3f,g and 4h-j) were prepared and investigated to see if they have more favorable fluorescence characteristics than the unconstrained systems 2 that were prepared in previous studies. Dye types 3 and 4 have relatively rigid conformations caused by the heteroatom (3f and 3g) or ethylene bridge (4h-j) linkers that preclude free rotation of the substituted-benzene molecular fragments. In the event, the new dye types 3 and 4 have longer lambda(max) (abs) (620-660 nm) and lambda(max) (fluor) (630-680 nm) values than compounds 2, They also exhibit higher extinction coefficients (>100 000 M (1) cm(-1) except for 3g). Their fluorescent quantum yields are high (up to 0.72 for 4j), with the exception of compound 3g, which has a quantum yield of only 0.05. The redox properties of dyes 3 and 4 have also been examined.
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页码:2900 / 2906
页数:7
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