Tris(4′-Nitrobiphenyl)amine─An Octupolar Chromophore with High Two-Photon Absorption Cross-Section and Its Application for Uncaging of Calcium Ions in the Near-Infrared Region

Linh Tran Bao Nguyen, Cheng Lin Wu, Tzu Chau Lin, Manabu Abe

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Compounds with high two-photon absorption (2PA) performance in the near-infrared region have attracted great attention because of their application in the material and biological science. In this study, we have developed a simple and novel octupolar chromophore, tris(4′-nitrobiphenyl)amine 1, with three nitro peripheral groups attached to a triphenylamine core via biphenyl linkers. A mono-branched analogue 2 has also been prepared to investigate the effects of octupolar and dipolar systems on photophysical and 2PA behaviors. Compound 1, despite having a much simpler structure than the previous three-branched scaffolds, exhibits comparable σ2values, reaching 1330 GM at 730 nm and 900 GM at 820 nm in toluene. Combined with an outstanding σ2/MW ratio (2.2 GM g-1mol) and a high fluorescence quantum yield (0.51), 1 displays potential as a promising two-photon (2P) probe for bioimaging. Subsequently, the ethylene glycol tetraacetic acid-substituted derivatives featuring octupolar (3 and 5) or dipolar (4 and 6) character have been synthesized and their one-photon (1P) and 2P photochemical reactions have been examined. Finally, 1P- and 2P-triggered uncaging of Ca2+from these calcium chelators has been confirmed.

Original languageEnglish
Pages (from-to)15888-15898
Number of pages11
JournalJournal of Organic Chemistry
Volume87
Issue number23
DOIs
StatePublished - 2 Dec 2022

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