Journal of Porphyrins and Phthalocyanines ( IF 1.5 ) Pub Date : 2023-06-14 , DOI: 10.1142/s1088424623500694 Kyo Yamagata 1 , Oscar Fernandez-Vera 1 , Shu Seki 1 , Takayuki Tanaka 1
Dianilinotripyrrin was condensed with phenylboronic acid at high temperature to give its phenylboron(III) complex in which the conjugation system changed to serve as a divalent ligand. As a result, two aniline moieties form an intramolecular hydrogen bond between the NH and iminic N sites, fixing the conformation to stand as a closed macrocycle. The structure of this macrocycle contains both cone-shaped boron center and helical terminal moieties. The twisted helical moieties can be perturbed by the substituents at the aniline moiety, while the optical properties are not drastically altered thereby. -Phenylene-bridged face-to-face dimer was also synthesized by the same approach, which exhibited negligible electronic communication between the chromophores.
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