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).
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.
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25 It was difficult to determine the dimerization association constants for 4a and 4b in CDCl3 because of almost complete association (i.e., Kd >103). A small difference between 4a and 4b might be ascribed to the steric repulsion between the trifluoromethyl group and tripyrrin core.
26 A preliminary measurement for the fluorescence lifetime using time-correlated single photon counting technique revealed the lifetime of 0.75 ns for 4b. See SI for details.
27
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Gautam R,
Curtis CJ,
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J. Phys. Chem. B 2019; 123: 5524
28 CCDC 2331837 (4a) and 2331836 (4b) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
