Crown ether functionalization of a porphyrin-based `molecular square': Induction of fluorescence sensitivity to alkali metal cations

Seung Hyun Chang; Kwang Bo Chung; Rovert V. Slone; Joseph T. Hupp

doi:10.1016/S0379-6779(00)00367-2

Crown ether functionalization of a porphyrin-based `molecular square': Induction of fluorescence sensitivity to alkali metal cations

Seung Hyun Chang, Kwang Bo Chung, Rovert V. Slone, Joseph T. Hupp

Chemistry

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

21 Scopus citations

Abstract

A porphyrin-based `molecular square' (1), prepared by reaction of a dipyridylporphyrin species with Re(CO)₅Cl and subsequently with Zn^II acetate, was functionalized with 2-(methylene-15-crown-5-ether)-nicotinoyl ester (2). Functionalization was achieved by axially ligating each of the four available Zn^II sites within the porphyrins. (2) was synthesized by reaction of 2-(hydroxymethyl)-15-crown-5-ether and nicotinoyl chloride in CH₂Cl₂. Functionalization renders the square's fluorescence emission intensity responsive to added Na⁺ and, to a lesser extent, K⁺.

Original language	English (US)
Pages (from-to)	215-217
Number of pages	3
Journal	Synthetic Metals
Volume	117
Issue number	1-3
DOIs	https://doi.org/10.1016/S0379-6779(00)00367-2
State	Published - Feb 15 2001

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Condensed Matter Physics
Mechanics of Materials
Mechanical Engineering
Metals and Alloys
Materials Chemistry

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title = "Crown ether functionalization of a porphyrin-based `molecular square': Induction of fluorescence sensitivity to alkali metal cations",

abstract = "A porphyrin-based `molecular square' (1), prepared by reaction of a dipyridylporphyrin species with Re(CO)5Cl and subsequently with ZnII acetate, was functionalized with 2-(methylene-15-crown-5-ether)-nicotinoyl ester (2). Functionalization was achieved by axially ligating each of the four available ZnII sites within the porphyrins. (2) was synthesized by reaction of 2-(hydroxymethyl)-15-crown-5-ether and nicotinoyl chloride in CH2Cl2. Functionalization renders the square's fluorescence emission intensity responsive to added Na+ and, to a lesser extent, K+.",

author = "Chang, {Seung Hyun} and Chung, {Kwang Bo} and Slone, {Rovert V.} and Hupp, {Joseph T.}",

note = "Funding Information: This work was supported in part by the Taegu University Research Grant, 1999, and by the US National Science Foundation (CHE-9810483). ",

year = "2001",

month = feb,

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doi = "10.1016/S0379-6779(00)00367-2",

language = "English (US)",

volume = "117",

pages = "215--217",

journal = "Synthetic Metals",

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TY - JOUR

T1 - Crown ether functionalization of a porphyrin-based `molecular square'

T2 - Induction of fluorescence sensitivity to alkali metal cations

AU - Chang, Seung Hyun

AU - Chung, Kwang Bo

AU - Slone, Rovert V.

AU - Hupp, Joseph T.

N1 - Funding Information: This work was supported in part by the Taegu University Research Grant, 1999, and by the US National Science Foundation (CHE-9810483).

PY - 2001/2/15

Y1 - 2001/2/15

N2 - A porphyrin-based `molecular square' (1), prepared by reaction of a dipyridylporphyrin species with Re(CO)5Cl and subsequently with ZnII acetate, was functionalized with 2-(methylene-15-crown-5-ether)-nicotinoyl ester (2). Functionalization was achieved by axially ligating each of the four available ZnII sites within the porphyrins. (2) was synthesized by reaction of 2-(hydroxymethyl)-15-crown-5-ether and nicotinoyl chloride in CH2Cl2. Functionalization renders the square's fluorescence emission intensity responsive to added Na+ and, to a lesser extent, K+.

AB - A porphyrin-based `molecular square' (1), prepared by reaction of a dipyridylporphyrin species with Re(CO)5Cl and subsequently with ZnII acetate, was functionalized with 2-(methylene-15-crown-5-ether)-nicotinoyl ester (2). Functionalization was achieved by axially ligating each of the four available ZnII sites within the porphyrins. (2) was synthesized by reaction of 2-(hydroxymethyl)-15-crown-5-ether and nicotinoyl chloride in CH2Cl2. Functionalization renders the square's fluorescence emission intensity responsive to added Na+ and, to a lesser extent, K+.

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