Synthesis and photodynamics of fluorescent blue bodipy-porphyrin tweezers linked by triazole rings

Antoine Eggenspiller; Atsuro Takai; Mohamed E. El-Khouly; Kei Ohkubo; Claude P. Gros; Claire Bernhard; Christine Goze; Franck Denat; Jean Michel Barbe; Shunichi Fukuzumi

doi:10.1021/jp300415a

Synthesis and photodynamics of fluorescent blue bodipy-porphyrin tweezers linked by triazole rings

Antoine Eggenspiller, Atsuro Takai, Mohamed E. El-Khouly, Kei Ohkubo, Claude P. Gros, Claire Bernhard, Christine Goze, Franck Denat, Jean Michel Barbe, Shunichi Fukuzumi

Department of Chemistry & Nanoscience

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

54 Scopus citations

Abstract

Novel zinc porphyrin tweezers in which two zinc porphyrins were connected with π-conjugated boron dipyrromethenes (BDP meso-Por ₂ and BDP β-Por ₂) through triazole rings were synthesized to investigate the photoinduced energy transfer and electron transfer. The UV-vis spectrum of BDP β-Por ₂ which has less bulky substituents than BDP meso-Por ₂ exhibits splitting of the Soret band as a result of the interaction between porphyrins of BDP β-Por ₂ in the excited state. Such interaction between porphyrins of both BDP β-Por ₂ and BDP meso-Por ₂ is dominant at room temperature, while the coordination of the nitrogen atoms of the triazole rings to the zinc ions of the porphyrins occurs at low temperature. The conformational change of the BDP-porphyrin composites was confirmed by the changes in UV-vis and fluorescence spectra depending on temperature. Photodynamics of BDP meso-Por ₂ and BDP β-Por ₂ has also been investigated by laser flash photolysis. Efficient singlet-singlet energy transfer from the ZnP to the π-conjugated BDP moiety of both BDP meso-Por ₂ and BDP β-Por ₂ occurred in opposite direction as compared to energy transfer from conventional BDP to ZnP due to the π-conjugation in nonpolar toluene. In polar benzonitrile, however, additional electron transfer occurred along with energy transfer.

Original language	English
Pages (from-to)	3889-3898
Number of pages	10
Journal	Journal of Physical Chemistry A
Volume	116
Issue number	15
DOIs	https://doi.org/10.1021/jp300415a
State	Published - 19 Apr 2012

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title = "Synthesis and photodynamics of fluorescent blue bodipy-porphyrin tweezers linked by triazole rings",

abstract = "Novel zinc porphyrin tweezers in which two zinc porphyrins were connected with π-conjugated boron dipyrromethenes (BDP meso-Por 2 and BDP β-Por 2) through triazole rings were synthesized to investigate the photoinduced energy transfer and electron transfer. The UV-vis spectrum of BDP β-Por 2 which has less bulky substituents than BDP meso-Por 2 exhibits splitting of the Soret band as a result of the interaction between porphyrins of BDP β-Por 2 in the excited state. Such interaction between porphyrins of both BDP β-Por 2 and BDP meso-Por 2 is dominant at room temperature, while the coordination of the nitrogen atoms of the triazole rings to the zinc ions of the porphyrins occurs at low temperature. The conformational change of the BDP-porphyrin composites was confirmed by the changes in UV-vis and fluorescence spectra depending on temperature. Photodynamics of BDP meso-Por 2 and BDP β-Por 2 has also been investigated by laser flash photolysis. Efficient singlet-singlet energy transfer from the ZnP to the π-conjugated BDP moiety of both BDP meso-Por 2 and BDP β-Por 2 occurred in opposite direction as compared to energy transfer from conventional BDP to ZnP due to the π-conjugation in nonpolar toluene. In polar benzonitrile, however, additional electron transfer occurred along with energy transfer.",

author = "Antoine Eggenspiller and Atsuro Takai and El-Khouly, {Mohamed E.} and Kei Ohkubo and Gros, {Claude P.} and Claire Bernhard and Christine Goze and Franck Denat and Barbe, {Jean Michel} and Shunichi Fukuzumi",

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doi = "10.1021/jp300415a",

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T1 - Synthesis and photodynamics of fluorescent blue bodipy-porphyrin tweezers linked by triazole rings

AU - Eggenspiller, Antoine

AU - Takai, Atsuro

AU - El-Khouly, Mohamed E.

AU - Ohkubo, Kei

AU - Gros, Claude P.

AU - Bernhard, Claire

AU - Goze, Christine

AU - Denat, Franck

AU - Barbe, Jean Michel

AU - Fukuzumi, Shunichi

PY - 2012/4/19

Y1 - 2012/4/19

N2 - Novel zinc porphyrin tweezers in which two zinc porphyrins were connected with π-conjugated boron dipyrromethenes (BDP meso-Por 2 and BDP β-Por 2) through triazole rings were synthesized to investigate the photoinduced energy transfer and electron transfer. The UV-vis spectrum of BDP β-Por 2 which has less bulky substituents than BDP meso-Por 2 exhibits splitting of the Soret band as a result of the interaction between porphyrins of BDP β-Por 2 in the excited state. Such interaction between porphyrins of both BDP β-Por 2 and BDP meso-Por 2 is dominant at room temperature, while the coordination of the nitrogen atoms of the triazole rings to the zinc ions of the porphyrins occurs at low temperature. The conformational change of the BDP-porphyrin composites was confirmed by the changes in UV-vis and fluorescence spectra depending on temperature. Photodynamics of BDP meso-Por 2 and BDP β-Por 2 has also been investigated by laser flash photolysis. Efficient singlet-singlet energy transfer from the ZnP to the π-conjugated BDP moiety of both BDP meso-Por 2 and BDP β-Por 2 occurred in opposite direction as compared to energy transfer from conventional BDP to ZnP due to the π-conjugation in nonpolar toluene. In polar benzonitrile, however, additional electron transfer occurred along with energy transfer.

AB - Novel zinc porphyrin tweezers in which two zinc porphyrins were connected with π-conjugated boron dipyrromethenes (BDP meso-Por 2 and BDP β-Por 2) through triazole rings were synthesized to investigate the photoinduced energy transfer and electron transfer. The UV-vis spectrum of BDP β-Por 2 which has less bulky substituents than BDP meso-Por 2 exhibits splitting of the Soret band as a result of the interaction between porphyrins of BDP β-Por 2 in the excited state. Such interaction between porphyrins of both BDP β-Por 2 and BDP meso-Por 2 is dominant at room temperature, while the coordination of the nitrogen atoms of the triazole rings to the zinc ions of the porphyrins occurs at low temperature. The conformational change of the BDP-porphyrin composites was confirmed by the changes in UV-vis and fluorescence spectra depending on temperature. Photodynamics of BDP meso-Por 2 and BDP β-Por 2 has also been investigated by laser flash photolysis. Efficient singlet-singlet energy transfer from the ZnP to the π-conjugated BDP moiety of both BDP meso-Por 2 and BDP β-Por 2 occurred in opposite direction as compared to energy transfer from conventional BDP to ZnP due to the π-conjugation in nonpolar toluene. In polar benzonitrile, however, additional electron transfer occurred along with energy transfer.

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Synthesis and photodynamics of fluorescent blue bodipy-porphyrin tweezers linked by triazole rings

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