4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes modified for extended conjugation and restricted bond rotations
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes modified for extended conjugation and restricted bond rotations
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DOI：
10.1021/jo991927o
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发表时间：
2000-05-19
影响因子：
3.6
通讯作者：
Burgess, K
中科院分区：
文献类型：
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作者：
Chen, J;Burghart, A;Burgess, K
制备并研究了五种新的受约束的芳基取代的4，4-二氟-4-硼杂-3a，4a-二氮杂-s-引达省（BODIPY）染料（3f、g和4 h-j），以观察它们是否具有比在先前研究中制备的无约束系统2更有利的荧光特性。染料类型3和4具有由杂原子（3f和3g）或亚乙基桥（4 h-j）接头引起的相对刚性的构象，其阻止取代的苯分子片段的自由旋转。结果表明，新型染料3和4具有比化合物2更长的λ（max）（abs）（620-660 nm）和λ（max）（fluor）（630-680 nm）值，它们还表现出更高的消光系数（除3g外>100 000 M（1）cm（-1））。它们的荧光量子产率都很高（4j高达0.72），除了化合物3g，其量子产率仅为0.05。染料3和4的氧化还原性能也已被检查。
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.