Journal of Photochemistry and Photobiology A: Chemistry, volume 349, pages 197-206

Enhance the fluorescence and singlet oxygen generation ability of BODIPY: Modification on the meso-phenyl unit with electron withdrawing groups

Zhang Xian Fu ^{1, 2}

Zhang Yakui ³

Liu Chang ¹

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Department of Materials Science and Engineering, Southern University of Science and Technology, Shenzhen, Guangdong Province, 518055, China |

Institute of Applied Photochemistry & Center of Instrumental Analysis, Hebei Normal University of Science and Technology, Qinhuangdao, Hebei Province, 066004, China |

Institute of Applied Photochemistry & Center of Instrumental Analysis, Hebei Normal University of Science and Technology, Qinhuangdao, Hebei Province 066004, China |

Publication type: Journal Article

Publication date: 2017-12-01

Elsevier

Journal: Journal of Photochemistry and Photobiology A: Chemistry

Quartile SCImago

Quartile WOS

Impact factor: 4.3

ISSN: 10106030, 18732666

DOI: 10.1016/j.jphotochem.2017.09.040

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General Chemistry

General Chemical Engineering

General Physics and Astronomy

Abstract

Herein, meso -R-carboxyphenyl substituted BODIPY compounds were synthesized and characterized (R = CH 3 , COOH, NO 2 , H and Br 4 ). The fluorescence, excited triplet state and singlet oxygen formation properties for these compounds were measured in nonpolar and polar solvents by UV–vis absorption, steady-state and time-resolved fluorescence methods, as well as laser flash photolysis technique. These BODIPYs exhibit very different fluorescence quantum yield and lifetime value, as well as singlet oxygen formation capability in polar solvents. In contrast, these compounds show very similar spectral shape and position, emit bright green fluorescence in non polar solvents. The introduction of an ortho -COOH on the benzene unit leads to a 20-fold increase in the fluorescence quantum yield. The further introduction of an electron withdrawing NO 2 or COOH on the phenyl makes the BODIPY dye show much higher capability to generate singlet oxygen (up to 5-fold increase) and causes a sharp decrease in both fluorescence quantum yield and lifetime value. The increase in solvent polarity enhances singlet oxygen generation and intramolecular fluorescence quenching. The results are explained by the presence of intramolecular photoinduced electron/charge transfer from BODIPY core to the carboxyphenyl moiety.

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Citations by journals

	1 2
Journal of Photochemistry and Photobiology A: Chemistry	Journal of Photochemistry and Photobiology A: Chemistry, 2, 11.76% Journal of Photochemistry and Photobiology A: Chemistry 2 publications, 11.76%
Inorganic Chemistry Communication	Inorganic Chemistry Communication, 1, 5.88% Inorganic Chemistry Communication 1 publication, 5.88%
Journal of Luminescence	Journal of Luminescence, 1, 5.88% Journal of Luminescence 1 publication, 5.88%
Molecules	Molecules, 1, 5.88% Molecules 1 publication, 5.88%
Journal of Fluorescence	Journal of Fluorescence, 1, 5.88% Journal of Fluorescence 1 publication, 5.88%
ChemMedChem	ChemMedChem, 1, 5.88% ChemMedChem 1 publication, 5.88%
Journal of Physical Organic Chemistry	Journal of Physical Organic Chemistry, 1, 5.88% Journal of Physical Organic Chemistry 1 publication, 5.88%
Chemical Reviews	Chemical Reviews, 1, 5.88% Chemical Reviews 1 publication, 5.88%
ChemPhotoChem	ChemPhotoChem, 1, 5.88% ChemPhotoChem 1 publication, 5.88%
Journal of Physical Chemistry B	Journal of Physical Chemistry B, 1, 5.88% Journal of Physical Chemistry B 1 publication, 5.88%
Journal of Physical Chemistry C	Journal of Physical Chemistry C, 1, 5.88% Journal of Physical Chemistry C 1 publication, 5.88%
ACS Applied Nano Materials	ACS Applied Nano Materials, 1, 5.88% ACS Applied Nano Materials 1 publication, 5.88%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 1, 5.88% Organic and Biomolecular Chemistry 1 publication, 5.88%
Supramolecular Chemistry	Supramolecular Chemistry, 1, 5.88% Supramolecular Chemistry 1 publication, 5.88%
Physical Chemistry Chemical Physics	Physical Chemistry Chemical Physics, 1, 5.88% Physical Chemistry Chemical Physics 1 publication, 5.88%
Chemistry - A European Journal	Chemistry - A European Journal, 1, 5.88% Chemistry - A European Journal 1 publication, 5.88%
	1 2

Citations by publishers

	1 2 3 4
Elsevier	Elsevier, 4, 23.53% Elsevier 4 publications, 23.53%
Wiley	Wiley, 4, 23.53% Wiley 4 publications, 23.53%
American Chemical Society (ACS)	American Chemical Society (ACS), 4, 23.53% American Chemical Society (ACS) 4 publications, 23.53%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 2, 11.76% Royal Society of Chemistry (RSC) 2 publications, 11.76%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 5.88% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 5.88%
Springer Nature	Springer Nature, 1, 5.88% Springer Nature 1 publication, 5.88%
Taylor & Francis	Taylor & Francis, 1, 5.88% Taylor & Francis 1 publication, 5.88%
	1 2 3 4

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Zhang X. F. et al. Enhance the fluorescence and singlet oxygen generation ability of BODIPY: Modification on the meso-phenyl unit with electron withdrawing groups // Journal of Photochemistry and Photobiology A: Chemistry. 2017. Vol. 349. pp. 197-206.

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Zhang X. F., Zhang Y., Liu C. Enhance the fluorescence and singlet oxygen generation ability of BODIPY: Modification on the meso-phenyl unit with electron withdrawing groups // Journal of Photochemistry and Photobiology A: Chemistry. 2017. Vol. 349. pp. 197-206.

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RIS Copy

TY - JOUR

DO - 10.1016/j.jphotochem.2017.09.040

UR - https://doi.org/10.1016%2Fj.jphotochem.2017.09.040

TI - Enhance the fluorescence and singlet oxygen generation ability of BODIPY: Modification on the meso-phenyl unit with electron withdrawing groups

T2 - Journal of Photochemistry and Photobiology A: Chemistry

AU - Zhang, Xian Fu

AU - Zhang, Yakui

AU - Liu, Chang

PY - 2017

DA - 2017/12/01 00:00:00

PB - Elsevier

SP - 197-206

VL - 349

SN - 1010-6030

SN - 1873-2666

ER -

BibTex

Cite this

BibTex Copy

@article{2017_Zhang,

author = {Xian Fu Zhang and Yakui Zhang and Chang Liu},

title = {Enhance the fluorescence and singlet oxygen generation ability of BODIPY: Modification on the meso-phenyl unit with electron withdrawing groups},

journal = {Journal of Photochemistry and Photobiology A: Chemistry},

year = {2017},

volume = {349},

publisher = {Elsevier},

month = {dec},

url = {https://doi.org/10.1016%2Fj.jphotochem.2017.09.040},

pages = {197--206},

doi = {10.1016/j.jphotochem.2017.09.040}

}

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Publisher

Elsevier

Journal

Journal of Photochemistry and Photobiology A: Chemistry

Quartile SCImago

Quartile WOS

Impact factor

4.3

ISSN

10106030 (Print)
18732666 (Electronic)