Acetylene and trans-Ethylene Bridged BIII-Subporphyrin Dimers

Yosuke Bekki; Seongsoo Kang; Dongho Kim; Atsuhiro Osuka

doi:10.1002/asia.201900547

Acetylene and trans-Ethylene Bridged B^III-Subporphyrin Dimers

Yosuke Bekki, Seongsoo Kang, Dongho Kim, Atsuhiro Osuka

Department of Chemistry

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

2 Citations (Scopus)

Abstract

Acetylene and trans-ethylene bridged B^III-subporphyrin dimers were synthesized by cross-coupling reactions of meso-bromo B^III subporphyrin. These dimers display perturbed and red-shifted absorption spectra reaching around 750 nm and fluorescence reaching at around 850 nm with high quantum yields of 0.39 and 0.47, respectively. DFT calculations have revealed that the HOMOs and the LUMOs of both dimers are spread over the two subporphyrin units as an indication of effective conjugation between the two subporphyrin units. The large Stokes shifts and characteristic pico-second time-resolved transient absorption spectra indicated that the S₁-states of the dimers relax with structural changes, which are larger for the trans-ethylene bridged dimer.

Original language	English
Pages (from-to)	2230-2234
Number of pages	5
Journal	Chemistry - An Asian Journal
Volume	14
Issue number	13
DOIs	https://doi.org/10.1002/asia.201900547
Publication status	Published - 2019 Jul 1

Bibliographical note

Funding Information:
This work at Kyoto was supported by Grant-in-Aid from JSPS for Scientific Research (A): 18H03910, Challenging Exploratory Research: 18K19074. The work at Yonsei was supported by the Global Research Laboratory (GRL) Program funded by the Ministry of Science, ICT & Future, Korea (2013K1A1A2A02050183). The authors thank to Prof. Dr. Yorimitsu at Kyoto University for HR-MS measurements.

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Biochemistry
Organic Chemistry

Access to Document

10.1002/asia.201900547

Cite this

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title = "Acetylene and trans-Ethylene Bridged BIII-Subporphyrin Dimers",

abstract = "Acetylene and trans-ethylene bridged BIII-subporphyrin dimers were synthesized by cross-coupling reactions of meso-bromo BIII subporphyrin. These dimers display perturbed and red-shifted absorption spectra reaching around 750 nm and fluorescence reaching at around 850 nm with high quantum yields of 0.39 and 0.47, respectively. DFT calculations have revealed that the HOMOs and the LUMOs of both dimers are spread over the two subporphyrin units as an indication of effective conjugation between the two subporphyrin units. The large Stokes shifts and characteristic pico-second time-resolved transient absorption spectra indicated that the S1-states of the dimers relax with structural changes, which are larger for the trans-ethylene bridged dimer.",

author = "Yosuke Bekki and Seongsoo Kang and Dongho Kim and Atsuhiro Osuka",

note = "Funding Information: This work at Kyoto was supported by Grant-in-Aid from JSPS for Scientific Research (A): 18H03910, Challenging Exploratory Research: 18K19074. The work at Yonsei was supported by the Global Research Laboratory (GRL) Program funded by the Ministry of Science, ICT & Future, Korea (2013K1A1A2A02050183). The authors thank to Prof. Dr. Yorimitsu at Kyoto University for HR-MS measurements. Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = jul,

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doi = "10.1002/asia.201900547",

language = "English",

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T1 - Acetylene and trans-Ethylene Bridged BIII-Subporphyrin Dimers

AU - Bekki, Yosuke

AU - Kang, Seongsoo

AU - Kim, Dongho

AU - Osuka, Atsuhiro

N1 - Funding Information: This work at Kyoto was supported by Grant-in-Aid from JSPS for Scientific Research (A): 18H03910, Challenging Exploratory Research: 18K19074. The work at Yonsei was supported by the Global Research Laboratory (GRL) Program funded by the Ministry of Science, ICT & Future, Korea (2013K1A1A2A02050183). The authors thank to Prof. Dr. Yorimitsu at Kyoto University for HR-MS measurements. Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/7/1

Y1 - 2019/7/1

N2 - Acetylene and trans-ethylene bridged BIII-subporphyrin dimers were synthesized by cross-coupling reactions of meso-bromo BIII subporphyrin. These dimers display perturbed and red-shifted absorption spectra reaching around 750 nm and fluorescence reaching at around 850 nm with high quantum yields of 0.39 and 0.47, respectively. DFT calculations have revealed that the HOMOs and the LUMOs of both dimers are spread over the two subporphyrin units as an indication of effective conjugation between the two subporphyrin units. The large Stokes shifts and characteristic pico-second time-resolved transient absorption spectra indicated that the S1-states of the dimers relax with structural changes, which are larger for the trans-ethylene bridged dimer.

AB - Acetylene and trans-ethylene bridged BIII-subporphyrin dimers were synthesized by cross-coupling reactions of meso-bromo BIII subporphyrin. These dimers display perturbed and red-shifted absorption spectra reaching around 750 nm and fluorescence reaching at around 850 nm with high quantum yields of 0.39 and 0.47, respectively. DFT calculations have revealed that the HOMOs and the LUMOs of both dimers are spread over the two subporphyrin units as an indication of effective conjugation between the two subporphyrin units. The large Stokes shifts and characteristic pico-second time-resolved transient absorption spectra indicated that the S1-states of the dimers relax with structural changes, which are larger for the trans-ethylene bridged dimer.

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