Excited state intramolecular proton transfer and photophysics of a new fluorenyl two-photon fluorescent probe

Alma R. Morales; Katherine J. Schafer-Hales; Cicerón O. Yanez; Mykhailo V. Bondar; Olga V. Przhonska; Adam I. Marcus; Kevin D. Belfield

doi:10.1002/cphc.200900032

Excited state intramolecular proton transfer and photophysics of a new fluorenyl two-photon fluorescent probe

Alma R. Morales, Katherine J. Schafer-Hales, Cicerón O. Yanez, Mykhailo V. Bondar, Olga V. Przhonska, Adam I. Marcus, Kevin D. Belfield

Research output: Contribution to journal › Article › peer-review

41 Scopus citations

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.

Original language	English (US)
Pages (from-to)	2073-2081
Number of pages	9
Journal	ChemPhysChem
Volume	10
Issue number	12
DOIs	https://doi.org/10.1002/cphc.200900032
State	Published - Aug 24 2009
Externally published	Yes

All Science Journal Classification (ASJC) codes

Atomic and Molecular Physics, and Optics
Physical and Theoretical Chemistry

Keywords

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

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10.1002/cphc.200900032

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title = "Excited state intramolecular proton transfer and photophysics of a new fluorenyl two-photon fluorescent probe",

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.",

keywords = "Bioimaging agents, Fluorescent probes, Hydrogen bonding, Photophysics, Two-photon induced fluorescence",

author = "Morales, {Alma R.} and Schafer-Hales, {Katherine J.} and Yanez, {Cicer{\'o}n O.} and Bondar, {Mykhailo V.} and Przhonska, {Olga V.} and Marcus, {Adam I.} and Belfield, {Kevin D.}",

note = "Funding Information: Acknowledgements: We thank K.V. Shcherbin for discussions and technical support. Financial support from Russian Foundation for Fundamental Studies (Grant 03-02-16083) is gratefully acknowledged.",

year = "2009",

month = aug,

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doi = "10.1002/cphc.200900032",

language = "English (US)",

volume = "10",

pages = "2073--2081",

journal = "ChemPhysChem",

issn = "1439-4235",

publisher = "Wiley-VCH Verlag",

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T1 - Excited state intramolecular proton transfer and photophysics of a new fluorenyl two-photon fluorescent probe

AU - Morales, Alma R.

AU - Schafer-Hales, Katherine J.

AU - Yanez, Cicerón O.

AU - Bondar, Mykhailo V.

AU - Przhonska, Olga V.

AU - Marcus, Adam I.

AU - Belfield, Kevin D.

N1 - Funding Information: Acknowledgements: We thank K.V. Shcherbin for discussions and technical support. Financial support from Russian Foundation for Fundamental Studies (Grant 03-02-16083) is gratefully acknowledged.

PY - 2009/8/24

Y1 - 2009/8/24

N2 - 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.

AB - 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.

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KW - Hydrogen bonding

KW - Photophysics

KW - Two-photon induced fluorescence

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Excited state intramolecular proton transfer and photophysics of a new fluorenyl two-photon fluorescent probe

Abstract

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