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Synthesis 2024; 56(13): 1999-2004
DOI: 10.1055/a-2314-1715
paper

Synthesis and Dynamic Behaviors of 5,7,8,10-Tetraphenyl-1,14-dianilinotripyrrins

Ayane Nishiyama
a   Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa Oiwake-cho, Sakyo-ku, Kyoto 606-8502, Japan
b   Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto 615-8510, Japan
,
Yusuke Matsuo
a   Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa Oiwake-cho, Sakyo-ku, Kyoto 606-8502, Japan
b   Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto 615-8510, Japan
,
Shu Seki∗
b   Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto 615-8510, Japan
,
Takayuki Tanaka  ∗
b   Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, Kyoto 615-8510, Japan
› Author AffiliationsThis work was supported by JSPS KAKENHI (Grant Numbers 21H05480, 22H00314 and 23K17942) and CREST, Japan Science and Technology Agency (JST).
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Abstract

5,7,8,10-Tetraphenyl-1,14-di(arylamino)tripyrrins have been synthesized via 5,7,8,10-tetraphenyltripyrrane. The structures and dynamic equilibrium between single helical monomer and double helical dimer were analyzed by 1H NMR spectra and X-ray diffraction analysis. Their dimerization association constants in CDCl3 are larger than those of previously reported dianilinotripyrrin derivatives. In DMSO, they exhibited luminescence around 700 nm as a consequence of restricted rotational relaxation by the phenyl groups installed at the 7,8-positions.

Key words

double helix - tripyrrin - dynamic equilibrium - luminescence - solvent effect - X-ray diffraction analysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2314-1715.
  • Supporting Information


Publication History

Received: 15 February 2024

Accepted after revision: 25 April 2024

Accepted Manuscript online:
25 April 2024

Article published online:
15 May 2024

© 2024. Thieme. All rights reserved

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