Design and synthesis of a new chromophore, 2-(4-nitrophenyl)benzofuran, for two-photon uncaging using near-IR light†,10.1039/C5CC07664A

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Design and synthesis of a new chromophore, 2-(4-nitrophenyl)benzofuran, for two-photon uncaging using near-IR light†

Naomitsu Komori,Ryusei Motoishi,Kenji Kamada,Ko Furukawa,Claudine Katan,Wakako Sawada,Noriko Takahashi

Chemical Communications Pub Date : 10/21/2015 00:00:00 , DOI:10.1039/C5CC07664A

Abstract

A new chromophore, 2-(4-nitrophenyl)benzofuran (NPBF), was designed for two-photon (TP) uncaging using near-IR light. The TP absorption (TPA) cross-sections of the newly designed NPBF chromophore were determined to be 18 GM at 720 nm and 54 GM at 740 nm in DMSO. The TP uncaging reaction of a caged benzoate with the NPBF chromophore quantitatively produced benzoic acid with an efficiency (δ_u) of ∼5.0 GM at 740 nm. The TP fragmentation of an EGTA unit was observed with δ_u = 16 GM. This behavior makes the new chromophore a promising TP photoremovable protecting group for physiological studies.