Structurally Isomerized Bis-Biphenyl Moieties Embedded in Hexaphyrin(3.1.1.3.1.1) and Octaphyrin(1.1.1.0.1.1.1.0)

Sangya Chitranshi; Mainak Das; B. Adinarayana; Won Young Cha; Dongho Kim; A. Srinivasan

doi:10.1021/acs.orglett.9b04614

Structurally Isomerized Bis-Biphenyl Moieties Embedded in Hexaphyrin(3.1.1.3.1.1) and Octaphyrin(1.1.1.0.1.1.1.0)

Sangya Chitranshi, Mainak Das, B. Adinarayana, Won Young Cha, Dongho Kim, A. Srinivasan

Department of Chemistry

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

6 Citations (Scopus)

Abstract

An o-p-biphenyl moiety-incorporated 32πhexaphyrin(3.1.1.3.1.1) is successfully achieved. Replacing ortho with meta connectivity in the biphenyl unit of hexaphyrin leads to the formation of its structural isomer, octaphyrin(1.1.1.0.1.1.1.0). Spectral and structural analyses reveal the lack of planarity in hexaphyrin and the presence of an m-arene unit in octaphyrin, thus affording nonaromatic characteristics.

Original language	English
Pages (from-to)	1081-1085
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.9b04614
Publication status	Published - 2020 Feb 7

Bibliographical note

Funding Information:
A.S. thanks NISER, Department of Atomic Energy, and SERB (EMR/2017/2932) for financial support. S.C. and M.D. thank NISER for the fellowship. The authors thank Dr. Pankaj Kalita (NISER) for determining the crystal structures of 4 ·2H + and 8 and Mr. Subhyan Chakraborty (NISER) for useful discussion regarding NMR.

Publisher Copyright:
Copyright © 2020 American Chemical Society.

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Structurally Isomerized Bis-Biphenyl Moieties Embedded in Hexaphyrin(3.1.1.3.1.1) and Octaphyrin(1.1.1.0.1.1.1.0)",

abstract = "An o-p-biphenyl moiety-incorporated 32πhexaphyrin(3.1.1.3.1.1) is successfully achieved. Replacing ortho with meta connectivity in the biphenyl unit of hexaphyrin leads to the formation of its structural isomer, octaphyrin(1.1.1.0.1.1.1.0). Spectral and structural analyses reveal the lack of planarity in hexaphyrin and the presence of an m-arene unit in octaphyrin, thus affording nonaromatic characteristics.",

author = "Sangya Chitranshi and Mainak Das and B. Adinarayana and Cha, {Won Young} and Dongho Kim and A. Srinivasan",

note = "Funding Information: A.S. thanks NISER, Department of Atomic Energy, and SERB (EMR/2017/2932) for financial support. S.C. and M.D. thank NISER for the fellowship. The authors thank Dr. Pankaj Kalita (NISER) for determining the crystal structures of 4 ·2H + and 8 and Mr. Subhyan Chakraborty (NISER) for useful discussion regarding NMR. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/acs.orglett.9b04614",

language = "English",

volume = "22",

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T1 - Structurally Isomerized Bis-Biphenyl Moieties Embedded in Hexaphyrin(3.1.1.3.1.1) and Octaphyrin(1.1.1.0.1.1.1.0)

AU - Chitranshi, Sangya

AU - Das, Mainak

AU - Adinarayana, B.

AU - Cha, Won Young

AU - Kim, Dongho

AU - Srinivasan, A.

N1 - Funding Information: A.S. thanks NISER, Department of Atomic Energy, and SERB (EMR/2017/2932) for financial support. S.C. and M.D. thank NISER for the fellowship. The authors thank Dr. Pankaj Kalita (NISER) for determining the crystal structures of 4 ·2H + and 8 and Mr. Subhyan Chakraborty (NISER) for useful discussion regarding NMR. Publisher Copyright: Copyright © 2020 American Chemical Society.

PY - 2020/2/7

Y1 - 2020/2/7

N2 - An o-p-biphenyl moiety-incorporated 32πhexaphyrin(3.1.1.3.1.1) is successfully achieved. Replacing ortho with meta connectivity in the biphenyl unit of hexaphyrin leads to the formation of its structural isomer, octaphyrin(1.1.1.0.1.1.1.0). Spectral and structural analyses reveal the lack of planarity in hexaphyrin and the presence of an m-arene unit in octaphyrin, thus affording nonaromatic characteristics.

AB - An o-p-biphenyl moiety-incorporated 32πhexaphyrin(3.1.1.3.1.1) is successfully achieved. Replacing ortho with meta connectivity in the biphenyl unit of hexaphyrin leads to the formation of its structural isomer, octaphyrin(1.1.1.0.1.1.1.0). Spectral and structural analyses reveal the lack of planarity in hexaphyrin and the presence of an m-arene unit in octaphyrin, thus affording nonaromatic characteristics.

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JO - Organic Letters

JF - Organic Letters

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Structurally Isomerized Bis-Biphenyl Moieties Embedded in Hexaphyrin(3.1.1.3.1.1) and Octaphyrin(1.1.1.0.1.1.1.0)

Abstract

Bibliographical note

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