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Synthesis of Boron(III)-Coordinated Subchlorophins and Their Peripheral Modifications
Kota Yoshida1, Wonhee Cha2, Dongho Kim2
1Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan.
Abstract:
A pyrrole-cleaving modification to transform boron(III) meso-triphenylsubporphyrin into boron(III) meso-triphenylsubchlorophin has been developed. Boron(III) subchlorophins thus synthesized show absorption and fluorescence spectra that are roughly similar to those of boron(III) subchlorins, but B-methoxy boron(III) subchlorophin showed considerably intensified fluorescence and a small Stokes shift. Peripheral modification reactions of B-phenyl boron(III) subchlorophin such as regioselective nitration with Cu(NO3 )2 ⋅3 H2 O, ipso-substitution reactions of boron(III) α-nitrosubchlorophin with CsF and CsCl, and Pd-catalyzed cross-coupling reactions of boron(III) α-chlorosubchlorophin with arylacetylenes, have been also explored to tune the optical properties of subchlorophins.
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