Non-symmetric thieno[3,2-b]thiophene-fused BODIPYs: synthesis, spectroscopic properties and providing a functional strategy for NIR probes
Non-symmetric thieno[3,2-b]thiophene-fused BODIPYs: synthesis, spectroscopic properties and providing a functional strategy for NIR probes
复制标题
非对称噻吩并[3,2-b]噻吩稠合 BODIPY：合成、光谱特性并为近红外探针提供功能策略
DOI：
10.1039/c9qo01190k
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发表时间：
2019-12-21
影响因子：
5.4
通讯作者：
Lu, Hua
中科院分区：
文献类型：
--
作者：
Sun, Yijuan;Yuan, Hao;Lu, Hua
Aromatic conjugation at the [beta] position is an efficient strategy to construct NIR BODIPY dyes; functionalization of such BODIPYs is difficult because of fewer modifiable positions. The methyl group at the 3,5-position can be versatilely functionalized by the Knoevenagel condensation reaction. In this paper, a small series of non-symmetric thieno[3,2-b]thiophene-fused BODIPYs have been prepared via the condensation of 7H-thieno[2 ',3 ':4,5]thieno[3,2-b]pyrrole-6-carbaldehydes and various pyrroles, followed by coordination with BF2. The resulting BODIPY dyes exhibited red absorption and emission with extremely high absorption coefficients (2 x 10(5) M-1 cm(-1)) and fluorescence quantum yields up to 1.00. Importantly, the remaining methyl group at the 3-position can be further functionalized to achieve NIR probes; we then synthesized an organosilicon-based probe for F- and evaluated its imaging in living cells. The structure-property relationships were interpreted on the basis of X-ray crystallography, optical spectroscopy and theoretical calculations.
