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Issue 17, 2014
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Synthesis of carbazole-based hetero-core-modified porphyrins

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Abstract

Cu(I)-mediated annulation reaction of a 1,1′-(1,3-butadiyne)-8,8′-(2,5-thiophene)-bridged carbazole dimer 10 with amines provided the N-substituted carbazole-based isophlorines 11a–11c. A similar annulation reaction with selenium in the presence of hydrazine monohydrate afforded hetero-core-modified isophlorine 12. The oxidation of 12 generated the corresponding 21-selena-23-thiaporphyrin 13, which exhibited NIR absorption. The intramolecular charge transfer from Se to S was confirmed by the 1H NMR results along with DFT calculations.

Graphical abstract: Synthesis of carbazole-based hetero-core-modified porphyrins

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Publication details

The article was received on 23 Dec 2013, accepted on 18 Feb 2014 and first published on 18 Feb 2014


Article type: Paper
DOI: 10.1039/C3OB42564A
Citation: Org. Biomol. Chem., 2014,12, 2656-2662
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    Synthesis of carbazole-based hetero-core-modified porphyrins

    C. Maeda, M. Masuda and N. Yoshioka, Org. Biomol. Chem., 2014, 12, 2656
    DOI: 10.1039/C3OB42564A

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