Abstract
The design and synthesis of two-photon-responsive chromophores have recently garnered significant attention owing to their potential applications in materials and life sciences. In this study, a novel π-conjugated system, 2-dimethylaminophenyl-5-nitrophenylthiophene derivatives, featuring a thiophene unit as the π-linker between the donor (NMe2C6H4–) and acceptor (NO2C6H4–) units was designed, synthesized, and applied for the development of two-photon-responsive chromophores as a photoremovable protecting group in the near-infrared region. Notably, the positional effect of the nitro group (NO2), meta versus para position, was observed in the uncaging process of benzoic acid. Additionally, while the para-isomer exhibited a single fluorescence peak, a dual emission was detected for the meta-isomer in polar solvents. The caged calcium ion (Ca2+) incorporating the newly synthesized thiophene unit exhibited a sizable two-photon absorption cross-section value (σ2 = 129 GM at 830 nm). Both one-photon and two-photon photoirradiation of caged calcium ions successfully released calcium ions, indicating the potential utility of 2,5-diarylthiophene derivatives in future biological studies.Graphical abstract
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