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Non-symmetric thieno[3,2-b]thiophene-fused BODIPYs: synthesis, spectroscopic properties and providing a functional strategy for NIR probes

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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.

Graphical abstract: Non-symmetric thieno[3,2-b]thiophene-fused BODIPYs: synthesis, spectroscopic properties and providing a functional strategy for NIR probes

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Publication details

The article was received on 27 Sep 2019, accepted on 23 Oct 2019 and first published on 28 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01190K
Org. Chem. Front., 2019, Advance Article

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    Non-symmetric thieno[3,2-b]thiophene-fused BODIPYs: synthesis, spectroscopic properties and providing a functional strategy for NIR probes

    Y. Sun, H. Yuan, L. Di, Z. Zhou, L. Gai, X. Xiao, W. He and H. Lu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01190K

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