Absorption, Fluorescence, and Two-Photon Excitation Ability of 5-o-Tolyl-11 (or 13)-o-tolylisoindolo[2,1-a]quinolines Prepared by Ring-Closing Metathesis and [2+3] Cycloaddition

Yuki Wada; Kwangkyun Jang; Hirokazu Ishii; Yuki Watakabe; Motosuke Tsutsumi; Makoto Sako; Tsunayoshi Takehara; Takeyuki Suzuki; Hirofumi Tsujino; Yasuo Tsutsumi; Tomomi Nemoto; Mitsuhiro Arisawa

doi:10.1002/asia.202401073

Absorption, Fluorescence, and Two-Photon Excitation Ability of 5-o-Tolyl-11 (or 13)-o-tolylisoindolo[2,1-a]quinolines Prepared by Ring-Closing Metathesis and [2+3] Cycloaddition

Chem Asian J. 2024 Nov 4:e202401073. doi: 10.1002/asia.202401073. Online ahead of print.

Authors

Affiliations

¹ Osaka University, Graduate School of Pharmaceutical Sciences, Suita, JAPAN.
² Osaka University, Graduate School of Pharmaceutical Sciences, JAPAN.
³ National Institutes of Natural Sciences - Okazaki Campus, National Institute for Physiological Sciences, JAPAN.
⁴ Osaka University, National Institute for Physiological Sciences, JAPAN.
⁵ Osaka University, SANKEN, JAPAN.
⁶ Osaka University, Graduate School of Pharmaceutical Sciences, 1-6 Yamada-oka, 565-0872, Suita, JAPAN.

PMID: 39495489
DOI: 10.1002/asia.202401073

Abstract

We have successfully improved the fluorescence quantum yield of isoindolo[2,1-a]quinoline derivatives by suppressing the rotation of the phenyl groups at positions 5 and 11 (or 13). Additionally, we found that the planarity of these phenyl groups at positions 5 and 13 of isoindolo[2,1-a]quinoline derivatives is crucial for two-photon absorption properties.

Keywords: Conformation analysis; Fluorescence; Nitrogen heterocycles.