Heteroleptic Tetrapyrrole-Fused Dimeric and Trimeric Skeletons with Unusual Non-Frustrated Fluorescence

Yuehong Zhang; Juwon Oh; Kang Wang; Chao Chen; Wei Cao; Kyu Hyung Park; Dongho Kim; Jianzhuang Jiang

doi:10.1002/chem.201504837

Heteroleptic Tetrapyrrole-Fused Dimeric and Trimeric Skeletons with Unusual Non-Frustrated Fluorescence

Yuehong Zhang, Juwon Oh, Kang Wang, Chao Chen, Wei Cao, Kyu Hyung Park, Dongho Kim, Jianzhuang Jiang

Department of Chemistry

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

12 Citations (Scopus)

Abstract

Phthalocyanine (Pc) and porphyrin (Por) chromophores have been fused through the benzo[α]pyrazine moiety, resulting in unprecedented heteroleptic tetrapyrrole-fused dimers and trimers. The heteroleptic tetrapyrrole nature has been clearly revealed based on single-crystal X-ray diffraction analysis of the zinc dimer. Electrochemical analysis, theoretical calculations, and time-resolved spectroscopic results disclose that the two/three-tetrapyrrole-fused skeletons behave as one totally π-conjugated system as a result of the strong conjugative interaction between/among the tetrapyrrole chromophores. In particular, the effectively extended π-electron system through the fused-bridge induced strong electronic communication between the Pc and Por moieties and large transition dipole moments in the Pc-Por-fused systems, providing high fluorescence quantum yields (>0.13) and relatively long excited state lifetimes (>1.3 ns) in comparison with their homo-tetrapyrrole-fused analogues.

Original language	English
Pages (from-to)	4492-4499
Number of pages	8
Journal	Chemistry - A European Journal
Volume	22
Issue number	13
DOIs	https://doi.org/10.1002/chem.201504837
Publication status	Published - 2016 Mar 18

Bibliographical note

Funding Information:
Financial support for the work at University of Science and Technology Beijing was from the National Key Basic Research Program of China (Grant Nos. 2013CB933402, 2012CB224801), National Natural Science Foundation of China (21401009 and 21290174), and Beijing Municipal Commission of Education. The work at Yonsei University has been financially supported by the Global Research Laboratory Program (2013K1A1A2A02050183).

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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10.1002/chem.201504837

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title = "Heteroleptic Tetrapyrrole-Fused Dimeric and Trimeric Skeletons with Unusual Non-Frustrated Fluorescence",

abstract = "Phthalocyanine (Pc) and porphyrin (Por) chromophores have been fused through the benzo[α]pyrazine moiety, resulting in unprecedented heteroleptic tetrapyrrole-fused dimers and trimers. The heteroleptic tetrapyrrole nature has been clearly revealed based on single-crystal X-ray diffraction analysis of the zinc dimer. Electrochemical analysis, theoretical calculations, and time-resolved spectroscopic results disclose that the two/three-tetrapyrrole-fused skeletons behave as one totally π-conjugated system as a result of the strong conjugative interaction between/among the tetrapyrrole chromophores. In particular, the effectively extended π-electron system through the fused-bridge induced strong electronic communication between the Pc and Por moieties and large transition dipole moments in the Pc-Por-fused systems, providing high fluorescence quantum yields (>0.13) and relatively long excited state lifetimes (>1.3 ns) in comparison with their homo-tetrapyrrole-fused analogues.",

author = "Yuehong Zhang and Juwon Oh and Kang Wang and Chao Chen and Wei Cao and Park, {Kyu Hyung} and Dongho Kim and Jianzhuang Jiang",

note = "Funding Information: Financial support for the work at University of Science and Technology Beijing was from the National Key Basic Research Program of China (Grant Nos. 2013CB933402, 2012CB224801), National Natural Science Foundation of China (21401009 and 21290174), and Beijing Municipal Commission of Education. The work at Yonsei University has been financially supported by the Global Research Laboratory Program (2013K1A1A2A02050183). Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

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AU - Zhang, Yuehong

AU - Oh, Juwon

AU - Wang, Kang

AU - Chen, Chao

AU - Cao, Wei

AU - Park, Kyu Hyung

AU - Kim, Dongho

AU - Jiang, Jianzhuang

N1 - Funding Information: Financial support for the work at University of Science and Technology Beijing was from the National Key Basic Research Program of China (Grant Nos. 2013CB933402, 2012CB224801), National Natural Science Foundation of China (21401009 and 21290174), and Beijing Municipal Commission of Education. The work at Yonsei University has been financially supported by the Global Research Laboratory Program (2013K1A1A2A02050183). Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2016/3/18

Y1 - 2016/3/18

N2 - Phthalocyanine (Pc) and porphyrin (Por) chromophores have been fused through the benzo[α]pyrazine moiety, resulting in unprecedented heteroleptic tetrapyrrole-fused dimers and trimers. The heteroleptic tetrapyrrole nature has been clearly revealed based on single-crystal X-ray diffraction analysis of the zinc dimer. Electrochemical analysis, theoretical calculations, and time-resolved spectroscopic results disclose that the two/three-tetrapyrrole-fused skeletons behave as one totally π-conjugated system as a result of the strong conjugative interaction between/among the tetrapyrrole chromophores. In particular, the effectively extended π-electron system through the fused-bridge induced strong electronic communication between the Pc and Por moieties and large transition dipole moments in the Pc-Por-fused systems, providing high fluorescence quantum yields (>0.13) and relatively long excited state lifetimes (>1.3 ns) in comparison with their homo-tetrapyrrole-fused analogues.

AB - Phthalocyanine (Pc) and porphyrin (Por) chromophores have been fused through the benzo[α]pyrazine moiety, resulting in unprecedented heteroleptic tetrapyrrole-fused dimers and trimers. The heteroleptic tetrapyrrole nature has been clearly revealed based on single-crystal X-ray diffraction analysis of the zinc dimer. Electrochemical analysis, theoretical calculations, and time-resolved spectroscopic results disclose that the two/three-tetrapyrrole-fused skeletons behave as one totally π-conjugated system as a result of the strong conjugative interaction between/among the tetrapyrrole chromophores. In particular, the effectively extended π-electron system through the fused-bridge induced strong electronic communication between the Pc and Por moieties and large transition dipole moments in the Pc-Por-fused systems, providing high fluorescence quantum yields (>0.13) and relatively long excited state lifetimes (>1.3 ns) in comparison with their homo-tetrapyrrole-fused analogues.

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Heteroleptic Tetrapyrrole-Fused Dimeric and Trimeric Skeletons with Unusual Non-Frustrated Fluorescence

Abstract

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