Tetrameric and Hexameric Porphyrin Nanorings: Template Synthesis and Photophysical Properties

Chihiro Maeda; Shoki Toyama; Naoki Okada; Kazuto Takaishi; Seongsoo Kang; Dongho Kim; Tadashi Ema

doi:10.1021/jacs.0c07707

Tetrameric and Hexameric Porphyrin Nanorings: Template Synthesis and Photophysical Properties

Chihiro Maeda, Shoki Toyama, Naoki Okada, Kazuto Takaishi, Seongsoo Kang, Dongho Kim, Tadashi Ema

Department of Chemistry

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

22 Citations (Scopus)

Abstract

Hexameric and tetrameric porphyrin nanorings, Z6T6 and Z4T4, were synthesized in 53% and 14% yields, respectively, by the Sonogashira-type self-oligomerization of porphyrin monomer 1 using hexadentate template T6 and tetrapyridylporphyrin template T4. Template-free nanorings Z6 and Z4 were also prepared. The femtosecond transient absorption measurements revealed fast excitation energy hopping (EEH) along these nanorings with hopping rates of 2-5 ps. Treatment of Z6 with chiral template CT6 gave Z6CT6 showing circular dichroism (CD) and circularly polarized luminescence (CPL) in the absorption and fluorescence regions of Z6, respectively, which indicates chirality transfer from CT6 to Z6.

Original language	English
Pages (from-to)	15661-15666
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	142
Issue number	37
DOIs	https://doi.org/10.1021/jacs.0c07707
Publication status	Published - 2020 Sept 16

Bibliographical note

Funding Information:
This work was supported by JSPS KAKENHI (Grant Number 15K13745) and Izumi Science and Technology Foundation. The work at Yonsei University was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (No. 2020R1A5A1019141).

Publisher Copyright:
Copyright © 2020 American Chemical Society.

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.0c07707

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title = "Tetrameric and Hexameric Porphyrin Nanorings: Template Synthesis and Photophysical Properties",

abstract = "Hexameric and tetrameric porphyrin nanorings, Z6T6 and Z4T4, were synthesized in 53% and 14% yields, respectively, by the Sonogashira-type self-oligomerization of porphyrin monomer 1 using hexadentate template T6 and tetrapyridylporphyrin template T4. Template-free nanorings Z6 and Z4 were also prepared. The femtosecond transient absorption measurements revealed fast excitation energy hopping (EEH) along these nanorings with hopping rates of 2-5 ps. Treatment of Z6 with chiral template CT6 gave Z6CT6 showing circular dichroism (CD) and circularly polarized luminescence (CPL) in the absorption and fluorescence regions of Z6, respectively, which indicates chirality transfer from CT6 to Z6.",

author = "Chihiro Maeda and Shoki Toyama and Naoki Okada and Kazuto Takaishi and Seongsoo Kang and Dongho Kim and Tadashi Ema",

note = "Funding Information: This work was supported by JSPS KAKENHI (Grant Number 15K13745) and Izumi Science and Technology Foundation. The work at Yonsei University was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (No. 2020R1A5A1019141). Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

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T2 - Template Synthesis and Photophysical Properties

AU - Maeda, Chihiro

AU - Toyama, Shoki

AU - Okada, Naoki

AU - Takaishi, Kazuto

AU - Kang, Seongsoo

AU - Kim, Dongho

AU - Ema, Tadashi

N1 - Funding Information: This work was supported by JSPS KAKENHI (Grant Number 15K13745) and Izumi Science and Technology Foundation. The work at Yonsei University was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (No. 2020R1A5A1019141). Publisher Copyright: Copyright © 2020 American Chemical Society.

PY - 2020/9/16

Y1 - 2020/9/16

N2 - Hexameric and tetrameric porphyrin nanorings, Z6T6 and Z4T4, were synthesized in 53% and 14% yields, respectively, by the Sonogashira-type self-oligomerization of porphyrin monomer 1 using hexadentate template T6 and tetrapyridylporphyrin template T4. Template-free nanorings Z6 and Z4 were also prepared. The femtosecond transient absorption measurements revealed fast excitation energy hopping (EEH) along these nanorings with hopping rates of 2-5 ps. Treatment of Z6 with chiral template CT6 gave Z6CT6 showing circular dichroism (CD) and circularly polarized luminescence (CPL) in the absorption and fluorescence regions of Z6, respectively, which indicates chirality transfer from CT6 to Z6.

AB - Hexameric and tetrameric porphyrin nanorings, Z6T6 and Z4T4, were synthesized in 53% and 14% yields, respectively, by the Sonogashira-type self-oligomerization of porphyrin monomer 1 using hexadentate template T6 and tetrapyridylporphyrin template T4. Template-free nanorings Z6 and Z4 were also prepared. The femtosecond transient absorption measurements revealed fast excitation energy hopping (EEH) along these nanorings with hopping rates of 2-5 ps. Treatment of Z6 with chiral template CT6 gave Z6CT6 showing circular dichroism (CD) and circularly polarized luminescence (CPL) in the absorption and fluorescence regions of Z6, respectively, which indicates chirality transfer from CT6 to Z6.

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Tetrameric and Hexameric Porphyrin Nanorings: Template Synthesis and Photophysical Properties

Abstract

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