Further insight into aryl nitration of tetraphenylporphyrin

Zhi Xue; Priscilla P.S. Lee; Yanming Wang; Daniel W J KWONG; Jing Li; John H. Xin; Rick W K WONG; Kevin K.L. Cheuk

doi:10.1016/j.tet.2011.06.031

Further insight into aryl nitration of tetraphenylporphyrin

Zhi Xue
, Priscilla P.S. Lee
, Yanming Wang
, Daniel W J KWONG
, Jing Li
, John H. Xin
, Rick W K WONG^*
, Kevin K.L. Cheuk

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

9 Citations (Scopus)

Abstract

We report an in-depth study on meso-aryl nitration of tetraphenylporphyrin. In contrast to previous studies, new evidence reveals that tetrakis(p- nitrophenyl) derivative can be obtained as a major product. Successful isolation of the barely soluble product toward a remarkable yield of nearly 90% has been reached by means of a solid phase extraction technique. Distribution of different nitro-porphyrin components is reassessed with respect to varying acid content in the reactions. An ortho-effect model is proposed to describe the formation mechanism.

Original language	English
Pages (from-to)	6030-6035
Number of pages	6
Journal	Tetrahedron
Volume	67
Issue number	33
DOIs	https://doi.org/10.1016/j.tet.2011.06.031
Publication status	Published - 19 Aug 2011

User-Defined Keywords

5,10,15,20-Tetrakis(4-nitrophenyl)-21H,23H-porphyrin
Nitration
Porphyrin functionalization
Porphyrin synthesis
Tetra-meso-phenylporphyrin

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10.1016/j.tet.2011.06.031

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@article{48dbcfdcb6e441c5badf463d643487d0,

title = "Further insight into aryl nitration of tetraphenylporphyrin",

abstract = "We report an in-depth study on meso-aryl nitration of tetraphenylporphyrin. In contrast to previous studies, new evidence reveals that tetrakis(p- nitrophenyl) derivative can be obtained as a major product. Successful isolation of the barely soluble product toward a remarkable yield of nearly 90\% has been reached by means of a solid phase extraction technique. Distribution of different nitro-porphyrin components is reassessed with respect to varying acid content in the reactions. An ortho-effect model is proposed to describe the formation mechanism.",

keywords = "5,10,15,20-Tetrakis(4-nitrophenyl)-21H,23H-porphyrin, Nitration, Porphyrin functionalization, Porphyrin synthesis, Tetra-meso-phenylporphyrin",

author = "Zhi Xue and Lee, \{Priscilla P.S.\} and Yanming Wang and KWONG, \{Daniel W J\} and Jing Li and Xin, \{John H.\} and WONG, \{Rick W K\} and Cheuk, \{Kevin K.L.\}",

note = "The work described in this paper was partially supported by the Research Grants Council of Hong Kong (Project Nos.: PolyU 5140/06E and 5136/07E). This project also benefited from the financial support of the University Grants Committee of Hong Kong (Grant Nos.: APH60, A-PD1N, A-PH94, A-PJ55, A-PK93, A-SA45, and J-BB6N).",

year = "2011",

month = aug,

day = "19",

doi = "10.1016/j.tet.2011.06.031",

language = "English",

volume = "67",

pages = "6030--6035",

journal = "Tetrahedron",

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T1 - Further insight into aryl nitration of tetraphenylporphyrin

AU - Xue, Zhi

AU - Lee, Priscilla P.S.

AU - Wang, Yanming

AU - KWONG, Daniel W J

AU - Li, Jing

AU - Xin, John H.

AU - WONG, Rick W K

AU - Cheuk, Kevin K.L.

N1 - The work described in this paper was partially supported by the Research Grants Council of Hong Kong (Project Nos.: PolyU 5140/06E and 5136/07E). This project also benefited from the financial support of the University Grants Committee of Hong Kong (Grant Nos.: APH60, A-PD1N, A-PH94, A-PJ55, A-PK93, A-SA45, and J-BB6N).

PY - 2011/8/19

Y1 - 2011/8/19

N2 - We report an in-depth study on meso-aryl nitration of tetraphenylporphyrin. In contrast to previous studies, new evidence reveals that tetrakis(p- nitrophenyl) derivative can be obtained as a major product. Successful isolation of the barely soluble product toward a remarkable yield of nearly 90% has been reached by means of a solid phase extraction technique. Distribution of different nitro-porphyrin components is reassessed with respect to varying acid content in the reactions. An ortho-effect model is proposed to describe the formation mechanism.

AB - We report an in-depth study on meso-aryl nitration of tetraphenylporphyrin. In contrast to previous studies, new evidence reveals that tetrakis(p- nitrophenyl) derivative can be obtained as a major product. Successful isolation of the barely soluble product toward a remarkable yield of nearly 90% has been reached by means of a solid phase extraction technique. Distribution of different nitro-porphyrin components is reassessed with respect to varying acid content in the reactions. An ortho-effect model is proposed to describe the formation mechanism.

KW - 5,10,15,20-Tetrakis(4-nitrophenyl)-21H,23H-porphyrin

KW - Nitration

KW - Porphyrin functionalization

KW - Porphyrin synthesis

KW - Tetra-meso-phenylporphyrin

UR - https://www.scopus.com/pages/publications/79960237665

U2 - 10.1016/j.tet.2011.06.031

DO - 10.1016/j.tet.2011.06.031

M3 - Journal article

AN - SCOPUS:79960237665

SN - 0040-4020

VL - 67

SP - 6030

EP - 6035

JO - Tetrahedron

JF - Tetrahedron

IS - 33

ER -

Further insight into aryl nitration of tetraphenylporphyrin

Abstract

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