Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing p-extended diarylacetylene motifs.
Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing p-extended diarylacetylene motifs.
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含有对位延伸二芳基乙炔基序的荧光 7-脱氮腺苷核苷的设计和合成。
DOI：
10.1039/c4ob02081b
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发表时间：
2015
影响因子：
3.2
通讯作者：
De Ornellas S
中科院分区：
文献类型：
--
作者：
De Ornellas S
已使用交叉偶联方法合成了含有二苯基乙炔部分的C-修饰的7-deazaadenosines。C-修饰的核苷表现出显著的荧光性质，包括高量子产率。溶致变色研究表明斯托克斯位移和溶剂极性之间的近线性相关性，这是分子内电荷转移的指示。DFT计算使我们能够将实验观察到的物理性质与一系列真实的和模型化合物内的计算的HOMO-LUMO能隙相关联。
C-modified 7-deazaadenosines containing a diphenylacetylene moiety have been synthesised using cross-coupling approaches. The C-modified nucleosides exhibit remarkable fluorescence properties, including high quantum yields. Solvatochromic studies show a near linear correlation between the Stokes shift and solvent polarity which is indicative of intramolecular charge transfer. DFT calculations have allowed us to correlate the experimentally observed photophysical properties with the calculated HOMO–LUMO energy gaps within a series of real and model compounds.