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

doi:10.1039/c7cc07170a

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

Applied Chemistry

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

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 language	English
Pages (from-to)	12258-12261
Number of pages	4
Journal	Chemical Communications
Volume	53
Issue number	91
DOIs	https://doi.org/10.1039/c7cc07170a
Publication status	Published - 2017

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c7cc07170a

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title = "The first synthesis of: Meso -dicycloalkylporphycenes: Ring strain effects on structural and optical properties of isomeric porphyrins",

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.",

author = "Toshikazu Ono and Daiki Koga and Kenji Yoza and Yoshio Hisaeda",

note = "Funding Information: This work was supported by JST PRESTO Grant Number JPMJPR1414. It was also supported by JSPS KAKENHI Grant Number JP16H04119 (Grant-in-Aid for Scientific Research (B) for Y. H.), JP17H04875 (Grant-in-Aid for Young Scientists (A) for T. O.), JP16H01035 (Precisely Designed Catalysts with Customized Scaffolding for Y. H.), and JP17H05161 (p-System Figuration for T. O.). We thank Ms Aiko Goto for the measurement of IR spectroscopy.",

year = "2017",

doi = "10.1039/c7cc07170a",

language = "English",

volume = "53",

pages = "12258--12261",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

number = "91",

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T2 - Meso -dicycloalkylporphycenes: Ring strain effects on structural and optical properties of isomeric porphyrins

AU - Ono, Toshikazu

AU - Koga, Daiki

AU - Yoza, Kenji

AU - Hisaeda, Yoshio

N1 - Funding Information: This work was supported by JST PRESTO Grant Number JPMJPR1414. It was also supported by JSPS KAKENHI Grant Number JP16H04119 (Grant-in-Aid for Scientific Research (B) for Y. H.), JP17H04875 (Grant-in-Aid for Young Scientists (A) for T. O.), JP16H01035 (Precisely Designed Catalysts with Customized Scaffolding for Y. H.), and JP17H05161 (p-System Figuration for T. O.). We thank Ms Aiko Goto for the measurement of IR spectroscopy.

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

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VL - 53

SP - 12258

EP - 12261

JO - Chemical Communications

JF - Chemical Communications

IS - 91

ER -

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

Abstract

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