Literature DB >> 19449363

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

Alma R Morales1, Katherine J Schafer-Hales, Ciceron O Yanez, Mykhailo V Bondar, Olga V Przhonska, Adam I Marcus, Kevin D Belfield.   

Abstract

The steady-state photophysical, NMR, and two-photon absorption (2PA) properties of a new n class="Chemical">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 approximately 600 GM, a sufficiently high value for two-photon fluorescence imaging. No dependence of two-photon 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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Year:  2009        PMID: 19449363      PMCID: PMC2763332          DOI: 10.1002/cphc.200900032

Source DB:  PubMed          Journal:  Chemphyschem        ISSN: 1439-4235            Impact factor:   3.102


  15 in total

1.  In situ incorporation of 2-(2-hydroxyphenyl)benzothiazole within FAU colloidal crystals.

Authors:  Svetlana Mintova; Vincent De Waele; Uli Schmidhammer; Eberhard Riedle; Thomas Bein
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-11       Impact factor: 15.336

2.  One- and two-photon fluorescence anisotropy of selected fluorene derivatives.

Authors:  K D Belfield; M V Bondar; J M Hales; A R Morales; O V Przhonska; K J Schafer
Journal:  J Fluoresc       Date:  2005-01       Impact factor: 2.217

3.  Charge instability in quadrupolar chromophores: symmetry breaking and solvatochromism.

Authors:  Francesca Terenziani; Anna Painelli; Claudine Katan; Marina Charlot; Mireille Blanchard-Desce
Journal:  J Am Chem Soc       Date:  2006-12-13       Impact factor: 15.419

4.  Synthesis and characterization of water-soluble two-photon excited blue fluorescent chromophores for bioimaging.

Authors:  Ali Hayek; Frédéric Bolze; Jean-François Nicoud; Patrice L Baldeck; Yves Mély
Journal:  Photochem Photobiol Sci       Date:  2005-11-11       Impact factor: 3.982

5.  A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging.

Authors:  Meng Zhang; Mengxiao Yu; Fuyou Li; Minwei Zhu; Manyu Li; Yanhong Gao; Lei Li; Zhiqiang Liu; Jianping Zhang; Dengqing Zhang; Tao Yi; Chunhui Huang
Journal:  J Am Chem Soc       Date:  2007-08-02       Impact factor: 15.419

6.  Video-rate far-field optical nanoscopy dissects synaptic vesicle movement.

Authors:  Volker Westphal; Silvio O Rizzoli; Marcel A Lauterbach; Dirk Kamin; Reinhard Jahn; Stefan W Hell
Journal:  Science       Date:  2008-02-21       Impact factor: 47.728

7.  Two-photon lifetime imaging of fluorescent probes in intact blood vessels: a window to sub-cellular structural information and binding status.

Authors:  Kim Douma; Remco T A Megens; Sietze Reitsma; Lenneke Prinzen; Dick W Slaaf; Marc A M J Van Zandvoort
Journal:  Microsc Res Tech       Date:  2007-05       Impact factor: 2.769

8.  Fluorene-based fluorescent probes with high two-photon action cross-sections for biological multiphoton imaging applications.

Authors:  Katherine J Schafer-Hales; Kevin D Belfield; Sheng Yao; Peter K Frederiksen; Joel M Hales; Pappachan E Kolattukudy
Journal:  J Biomed Opt       Date:  2005 Sep-Oct       Impact factor: 3.170

9.  Two-photon photochromism of a diarylethene enhanced by Förster resonance energy transfer from two-photon absorbing fluorenes.

Authors:  Kevin D Belfield; Mykhailo V Bondar; Claudia C Corredor; Florencio E Hernandez; Olga V Przhonska; Sheng Yao
Journal:  Chemphyschem       Date:  2006-12-11       Impact factor: 3.102

10.  One-and two-photon photostability of 9,9-didecyl-2-7-bis(N,N-diphenlamino)fluorene.

Authors:  Kevin D Belfield; Mykhailo V Bondar; Olga Przhonska; Katherine J Schafer
Journal:  Photochem Photobiol Sci       Date:  2004-01       Impact factor: 3.982

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  5 in total

1.  A series of carbazole cationic compounds with large two-photon absorption cross sections for imaging mitochondria in living cells with two-photon fluorescence microscopy.

Authors:  Xin Liu; Yuming Sun; Yuanhong Zhang; Ning Zhao; Hongshi Zhao; Guancong Wang; Xiaoqiang Yu; Hong Liu
Journal:  J Fluoresc       Date:  2010-10-16       Impact factor: 2.217

2.  Fluorene-based metal-ion sensing probe with high sensitivity to Zn2+ and efficient two-photon absorption.

Authors:  Kevin D Belfield; Mykhailo V Bondar; Andrew Frazer; Alma R Morales; Oleksiy D Kachkovsky; Ivan A Mikhailov; Artëm E Masunov; Olga V Przhonska
Journal:  J Phys Chem B       Date:  2010-07-22       Impact factor: 2.991

3.  Two-photon STED spectral determination for a new V-shaped organic fluorescent probe with efficient two-photon absorption.

Authors:  Kevin D Belfield; Mykhailo V Bondar; Alma R Morales; Lazaro A Padilha; Olga V Przhonska; Xuhua Wang
Journal:  Chemphyschem       Date:  2011-08-19       Impact factor: 3.102

4.  Luminescent Fluorene-Based Bis-Pyrazolyl Aniline Ligand for Aluminum Detection.

Authors:  Andrew Frazer; Alma R Morales; Adam W Woodward; Paul Tongwa; Tatiana Timofeeva; Kevin D Belfield
Journal:  J Fluoresc       Date:  2013-09-29       Impact factor: 2.217

5.  Two-photon absorption and time-resolved stimulated emission depletion spectroscopy of a new fluorenyl derivative.

Authors:  Kevin D Belfield; Mykhailo V Bondar; Alma R Morales; Xiling Yue; Gheorghe Luchita; Olga V Przhonska; Olexy D Kachkovsky
Journal:  Chemphyschem       Date:  2012-08-07       Impact factor: 3.102

  5 in total

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