Synthesis, characterization, energy transfer and photophysical properties of ethynyl bridge linked porphyrin-naphthalimide pentamer and its metal complexes

Zhijie Xu; Qunbo Mei; Qingfang Hua; Ruqiang Tian; Jiena Weng; Yujie Shi; Wei Huang

doi:10.1016/j.molstruc.2015.03.005

Synthesis, characterization, energy transfer and photophysical properties of ethynyl bridge linked porphyrin-naphthalimide pentamer and its metal complexes

Zhijie Xu, Qunbo Mei, Qingfang Hua, Ruqiang Tian, Jiena Weng, Yujie Shi, Wei Huang

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

17 Scopus citations

Abstract

Abstract A novel ethynyl bridge linked naphthalimide-functionized porphyrin TANPH₂ has been synthesized by a combination of Sonogashira coupling and Gonsalves and Pereira nitrobenzene reaction, and the corresponding metal (Zn²⁺ and Cu²⁺) complexes TANPZn and TANPCu were synthesized. The structures of these compounds were characterized by ¹H and ¹³C NMR spectra, FT-IR, MALDI-TOF-MS and elemental analysis. The photophysical properties have been investigated by UV-Vis absorption and steady-state fluorescence spectroscopy. Energy transfer studies have revealed that the excitation energy transfer occurred from the naphthalimide units to the porphyrin core. By the introduction of ethynyl bridges between the peripheral naphthalimide arms and the porphyrin core, TANPH₂ and TANPZn can emit intense red light with high fluorescent quantum yields.

Original language	English
Article number	21389
Pages (from-to)	1-8
Number of pages	8
Journal	Journal of Molecular Structure
Volume	1094
DOIs	https://doi.org/10.1016/j.molstruc.2015.03.005
State	Published - 15 Aug 2015
Externally published	Yes

Keywords

Energy transfer
Ethynyl bridge
Light harvesting
Naphthalimide
Porphyrin

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10.1016/j.molstruc.2015.03.005

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@article{417232da913843b2ae76758bcba3067b,

title = "Synthesis, characterization, energy transfer and photophysical properties of ethynyl bridge linked porphyrin-naphthalimide pentamer and its metal complexes",

abstract = "Abstract A novel ethynyl bridge linked naphthalimide-functionized porphyrin TANPH2 has been synthesized by a combination of Sonogashira coupling and Gonsalves and Pereira nitrobenzene reaction, and the corresponding metal (Zn2+ and Cu2+) complexes TANPZn and TANPCu were synthesized. The structures of these compounds were characterized by 1H and 13C NMR spectra, FT-IR, MALDI-TOF-MS and elemental analysis. The photophysical properties have been investigated by UV-Vis absorption and steady-state fluorescence spectroscopy. Energy transfer studies have revealed that the excitation energy transfer occurred from the naphthalimide units to the porphyrin core. By the introduction of ethynyl bridges between the peripheral naphthalimide arms and the porphyrin core, TANPH2 and TANPZn can emit intense red light with high fluorescent quantum yields.",

keywords = "Energy transfer, Ethynyl bridge, Light harvesting, Naphthalimide, Porphyrin",

author = "Zhijie Xu and Qunbo Mei and Qingfang Hua and Ruqiang Tian and Jiena Weng and Yujie Shi and Wei Huang",

year = "2015",

month = aug,

day = "15",

doi = "10.1016/j.molstruc.2015.03.005",

language = "英语",

volume = "1094",

pages = "1--8",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - Synthesis, characterization, energy transfer and photophysical properties of ethynyl bridge linked porphyrin-naphthalimide pentamer and its metal complexes

AU - Xu, Zhijie

AU - Mei, Qunbo

AU - Hua, Qingfang

AU - Tian, Ruqiang

AU - Weng, Jiena

AU - Shi, Yujie

AU - Huang, Wei

PY - 2015/8/15

Y1 - 2015/8/15

N2 - Abstract A novel ethynyl bridge linked naphthalimide-functionized porphyrin TANPH2 has been synthesized by a combination of Sonogashira coupling and Gonsalves and Pereira nitrobenzene reaction, and the corresponding metal (Zn2+ and Cu2+) complexes TANPZn and TANPCu were synthesized. The structures of these compounds were characterized by 1H and 13C NMR spectra, FT-IR, MALDI-TOF-MS and elemental analysis. The photophysical properties have been investigated by UV-Vis absorption and steady-state fluorescence spectroscopy. Energy transfer studies have revealed that the excitation energy transfer occurred from the naphthalimide units to the porphyrin core. By the introduction of ethynyl bridges between the peripheral naphthalimide arms and the porphyrin core, TANPH2 and TANPZn can emit intense red light with high fluorescent quantum yields.

AB - Abstract A novel ethynyl bridge linked naphthalimide-functionized porphyrin TANPH2 has been synthesized by a combination of Sonogashira coupling and Gonsalves and Pereira nitrobenzene reaction, and the corresponding metal (Zn2+ and Cu2+) complexes TANPZn and TANPCu were synthesized. The structures of these compounds were characterized by 1H and 13C NMR spectra, FT-IR, MALDI-TOF-MS and elemental analysis. The photophysical properties have been investigated by UV-Vis absorption and steady-state fluorescence spectroscopy. Energy transfer studies have revealed that the excitation energy transfer occurred from the naphthalimide units to the porphyrin core. By the introduction of ethynyl bridges between the peripheral naphthalimide arms and the porphyrin core, TANPH2 and TANPZn can emit intense red light with high fluorescent quantum yields.

KW - Energy transfer

KW - Ethynyl bridge

KW - Light harvesting

KW - Naphthalimide

KW - Porphyrin

UR - http://www.scopus.com/inward/record.url?scp=84927641562&partnerID=8YFLogxK

U2 - 10.1016/j.molstruc.2015.03.005

DO - 10.1016/j.molstruc.2015.03.005

M3 - 文章

AN - SCOPUS:84927641562

SN - 0022-2860

VL - 1094

SP - 1

EP - 8

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

M1 - 21389

ER -

Synthesis, characterization, energy transfer and photophysical properties of ethynyl bridge linked porphyrin-naphthalimide pentamer and its metal complexes

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Keywords

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