Asymmetric and Symmetric S-zig-zag-Fused BODIPYs: Synthesis and Photophysical and Oxidative Properties

• DOI: 10.1021/acs.joc.5c00508
• Publication Date: 2025-04-19T01:43:26Z
• Authors: Ruihan Yang; Lu Li; Shulin Gao; Zhehui Weng; WeiLi Li; Zhaohui Wang; Xiangguang Li; Yanhua Yang; Wei Jiang
• Keywords: Zigzag

We present a new, straightforward, and versatile approach that utilizes regioselective brominated precursors to synthesize both asymmetric symmetric S-zig-zag-fused BODIPYs (s-TFB bis-TFB) in moderate yields (45% 40%, respectively). X-ray structure analyses reveal the planar rigidity of BODIPY skeleton is progressively enhanced with an increasing number thiopyran rings. The annulation S-heteroaromatic rings at zig-zag edge core results blue-shifted absorption emission spectra, bis-TFB exhibiting maxima 530 539 nm elevated LUMO energy levels. In contrast, oxidation s-TFB m-CPBA demonstrates significant site selectivity, affording four products, namely s-s-SFB, s-bis-SFB, bis-s-SFB, bis-bis-SFB, ranging from 22% 36%. These oxidated derivatives display large red-shifted spectra (e.g., 648 735 for s-bis-SFB), along more stable HOMO levels reduced HOMO-LUMO gaps. This cyclization/oxidation strategy enables precise tuning optoelectronic properties, opening new avenues dye design application.