Title

Excited State Intramolecular Proton Transfer And Photophysics Of A New Fluorenyl Two-Photon Fluorescent Probe

Keywords

Bioimaging agents; Fluorescent probes; Hydrogen bonding; Photophysics; Two-photon induced fluorescence

Abstract

The steady-state photophysical, NMR, and two-photon absorption (2PA) properties of a new fluorene derivative (1) containing the 2-{2'-hydroxyphenyl) benzothiazole (HBT) terminal construct is investigated for use as a fluorescence probe in bioimaging. A comprehensive analysis of the linear spectral properties reveals inter- and intramolecular hydrogen bonding and excited state intramolecular proton transfer (ESIPT) processes in the HBT substituent. A specific electronic model with a double minimum potential energy surface is consistent with the observed spectral properties. The 2PA spectra are obtained using a standard two-photon induced fluorescence method with a femtosecond kHz laser system, affording a maximum 2PA cross section of -600 GM, a sufficiently high value for two-photon fluorescence imaging. No dependence of twophoton absorption efficiency on solvent properties and hydrogen bonding in the HBT substituent is observed. The potential use of this fluorenyl probe in bioimaging is demonstrated via one- and two-photon fluorescence imaging of COS-7 cells. © 2009 Wiley-VCH Verlag GmbH&Co. KGaA.

Publication Date

8-24-2009

Publication Title

ChemPhysChem

Volume

10

Issue

12

Number of Pages

2073-2081

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1002/cphc.200900032

Socpus ID

68949099598 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/68949099598

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