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

Naomitsu Komori; Satish Jakkampudi; Ryusei Motoishi; Manabu Abe; Kenji Kamada; Ko Furukawa; Claudine Katan; Wakako Sawada; Noriko Takahashi; Haruo Kasai; Bing Xue; Takayoshi Kobayashi

doi:10.1039/C5CC07664A

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

Naomitsu Komori,^a Satish Jakkampudi,^ab Ryusei Motoishi,^a Manabu Abe,*^abc Kenji Kamada,*^d Ko Furukawa,^e Claudine Katan,

*^f Wakako Sawada,^g Noriko Takahashi,^g Haruo Kasai,^bg Bing Xue^bh and Takayoshi Kobayashi^bh

Author affiliations

* Corresponding authors

^a Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-hiroshima, Hiroshima 739-8526, Japan
E-mail: mabe@hiroshima-u.ac.jp

^b JST-CREST, K’s Gobancho, 7, Gobancho, Chiyoda-ku, Tokyo 102-0076, Japan

^c Research Centre for Smart Materials, Hiroshima University, 1-3-1 Kagamiyama, Higashi-hiroshima, Hiroshima 739-8526, Japan

^d IFMRI, National Institute of Advanced Industrial Science and Technology (AIST), 1-8-31 Midorigaoka, Ikeda, Osaka 563-8577, Japan
E-mail: k.kamada@aist.go.jp

^e Centre for Instrumental Analysis, Niigata University, 8050 Ikarashi 2-no-cho, Nishi-ku, Niigata 950-2181, Japan

^f Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Universite Rennes 1, 35042 Rennes, France
E-mail: claudine.katan@univ-rennes1.fr

^g Laboratory of Structural Physiology, CDBIM, Graduate School of Medicine, The University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan

^h Advanced Ultrafast Laser Research Center, The University of Electro-Communications, Chofugaoka 1-5-1, Chofu, Tokyo 182-8585, Japan

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.

Chemical Communications

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

Abstract

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

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