The first synthesis of meso-dicycloalkylporphycenes: ring strain effects on structural and optical properties of isomeric porphyrins

Toshikazu Ono, Daiki Koga, Kenji Yoza, Yoshio Hisaeda

Research output: Contribution to journalArticle

Abstract

Two novel meso-dicycloalkylporphycenes, namely meso-dicyclopentyl- (Cy5Pc) and meso-dicyclohexylporphycenes (Cy6Pc) are synthesized for the first time in porphycene chemistry. We use intermolecular oxidative coupling of 5,6-dicycloalkydipyrroethenes mediated by hypervalent iodine(iii) reagents. The solution fluorescence maxima of Cy5Pc are more than 400 times as intense as that of Cy6Pc. The results suggested that photoluminescence switching is achieved through the ring strain perturbation of the meso-substituted cycloalkyl groups on the porphycene cavity.

Original languageEnglish
Pages (from-to)12258-12261
Number of pages4
JournalChemical Communications
Volume53
Issue number91
DOIs
Publication statusPublished - Nov 14 2017

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Porphyrins
Iodine
Structural properties
Photoluminescence
Optical properties
Fluorescence
porphycene

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The first synthesis of meso-dicycloalkylporphycenes : ring strain effects on structural and optical properties of isomeric porphyrins. / Ono, Toshikazu; Koga, Daiki; Yoza, Kenji; Hisaeda, Yoshio.

In: Chemical Communications, Vol. 53, No. 91, 14.11.2017, p. 12258-12261.

Research output: Contribution to journalArticle

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