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Tailoring C‑6-Substituted Coumarin Scaffolds for Novel Photophysical Properties and Stimuli-Responsive Chromism

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journal contribution
posted on 2021-10-11, 20:31 authored by Ravinder Singh, Deng-Gao Chen, Chun-Hsiang Wang, Yi-Cheng Lan, Yi-Hung Liu, Pi-Tai Chou, Chao-Tsen Chen
A judicious strategy was utilized to envision the substantial regio-positional effects of substituents on the photophysical properties of the 2H-chromen-2-one-3-benzothiazole scaffold-based push–pull framework, named 6-X-CUMs. Among them, 6-NEt2-CUM reveals prominent excited-state intramolecular charge transfer with a large change of dipole moment (Δμ ∼ 18.23 D), hence displaying remarkable emission solvatochromism from the green (536 nm in cyclohexane) to far-red region (714 nm in dimethyl sulfoxide) and a high-temperature sensitivity (−0.23 nm °C–1). These, together with unique basicity and acido-/vaporchromism upon acidification elucidated by NMR and photospectroscopic studies, show stark contrast to the conventional 7-NEt2-CUM. The new series of these tailored 6-X-CUMs represents a new dimension in tailoring the photophysical properties for the development of a promising class of multistimuli-responsive materials.

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