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Updated: Oct 17, 2025

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Tailoring C-6-Substituted Coumarin Scaffolds for Novel Photophysical Properties and Stimuli-Responsive Chromism
Ravinder Singh1, Deng-Gao Chen1, Chun-Hsiang Wang1
1Department of Chemistry, National Taiwan University, Taipei, 10617 Taiwan, ROC.
Abstract:
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-NEt-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-NEt-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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