Non-symmetric thieno[3,2-b]thiophene-fused BODIPYs: synthesis, spectroscopic properties and providing a functional strategy for NIR probes
- 28 October 2019
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic Chemistry Frontiers
- Vol. 6 (24), 3961-3968
- https://doi.org/10.1039/c9qo01190k
Abstract
Aromatic conjugation at the [β] 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 × 105 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.Keywords
Funding Information
- National Natural Science Foundation of China (21801057, 21871072)
- Hangzhou Normal University (2018PYXML009, 2018QDL002, 2018YLXK16)
- State Key Laboratory of Coordination Chemistry (SKLCC1813)
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