pi-Extended Coumarins Derived with Nonhydrolyzable Iminophosphoranes as Two-Photon-Excited Fluorophores

Liang-Yu Hsia, Hsin-Ni Chen, Chun-Hao Chiang, Ming-Yang Hung, Hao-Keng Wei, Chih-Wei Luo, Ming-Yu Kuo, Shun-Yuan Luo*, Chih-Chien Chu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

Novel coumarin-iminophosphorane (IPP) fluorophores that have stable resonance contributions from aza-ylides were formed by using the nonhydrolysis Staudinger reaction. The N=P formation reaction kinetics obey the conventional Staudinger reaction. The absorption and emission profiles of the coumarin-IPP derivatives can be fine-tuned: an electron-donating group at PPh3 enhances absorption and fluorescence, whereas an electron-withdrawing group at C-3 drives absorption and emission peaks toward blue-light wavelengths. Two-photon adsorption, accompanied by anti-Stokes fluorescence, is achieved under near-infrared femtosecond laser excitation.

Original languageEnglish
Pages (from-to)9361-9366
Number of pages6
JournalJournal of Organic Chemistry
Volume85
Issue number14
DOIs
StatePublished - 17 Jul 2020

Keywords

  • STAUDINGER REACTION
  • AZIDES
  • ACID

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