Asymmetric phthalocyanine synthesi by ROMP-capture-release

Xiaochun Chen; Thaddeus R. Salmon; Dominic V. McGrath

doi:10.1021/ol900352f

Asymmetric phthalocyanine synthesi by ROMP-capture-release

Xiaochun Chen
, Thaddeus R. Salmon
, Dominic V. McGrath

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

12 Scopus citations

Abstract

Statistical condensation of norbornenyl-tagged phthalonitrile 3 (Pn A) and 4,5-di-4-methoxyphenoxyphthalonitrile 4 (Pn B) followed by ring-opening metathesis polymerization (ROMP) of Pcs AB ₃ and B ₄ produced asymmetric Pc-appended polymers. Acidic cleavage of the resulting polymers afforded 2,3,9,10,16,17-hexa-(4-methoxyphenoxy)-23-hydroxy Pc 9. A more soluble 2,3,9,10,16,17-hexa-4-pentylphenoxy-23-hydroxy Pc 13 was synthesized by the same strategy and modified with sebacoyl chloride demonstrating that the unmasked hydroxyl site is reactive as a nucleophile.

Original language	English (US)
Pages (from-to)	2061-2064
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	10
DOIs	https://doi.org/10.1021/ol900352f
State	Published - May 21 2009

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol900352f

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title = "Asymmetric phthalocyanine synthesi by ROMP-capture-release",

abstract = "Statistical condensation of norbornenyl-tagged phthalonitrile 3 (Pn A) and 4,5-di-4-methoxyphenoxyphthalonitrile 4 (Pn B) followed by ring-opening metathesis polymerization (ROMP) of Pcs AB 3 and B 4 produced asymmetric Pc-appended polymers. Acidic cleavage of the resulting polymers afforded 2,3,9,10,16,17-hexa-(4-methoxyphenoxy)-23-hydroxy Pc 9. A more soluble 2,3,9,10,16,17-hexa-4-pentylphenoxy-23-hydroxy Pc 13 was synthesized by the same strategy and modified with sebacoyl chloride demonstrating that the unmasked hydroxyl site is reactive as a nucleophile.",

author = "Xiaochun Chen and Salmon, \{Thaddeus R.\} and McGrath, \{Dominic V.\}",

year = "2009",

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doi = "10.1021/ol900352f",

language = "English (US)",

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journal = "Organic Letters",

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T1 - Asymmetric phthalocyanine synthesi by ROMP-capture-release

AU - Chen, Xiaochun

AU - Salmon, Thaddeus R.

AU - McGrath, Dominic V.

PY - 2009/5/21

Y1 - 2009/5/21

N2 - Statistical condensation of norbornenyl-tagged phthalonitrile 3 (Pn A) and 4,5-di-4-methoxyphenoxyphthalonitrile 4 (Pn B) followed by ring-opening metathesis polymerization (ROMP) of Pcs AB 3 and B 4 produced asymmetric Pc-appended polymers. Acidic cleavage of the resulting polymers afforded 2,3,9,10,16,17-hexa-(4-methoxyphenoxy)-23-hydroxy Pc 9. A more soluble 2,3,9,10,16,17-hexa-4-pentylphenoxy-23-hydroxy Pc 13 was synthesized by the same strategy and modified with sebacoyl chloride demonstrating that the unmasked hydroxyl site is reactive as a nucleophile.

AB - Statistical condensation of norbornenyl-tagged phthalonitrile 3 (Pn A) and 4,5-di-4-methoxyphenoxyphthalonitrile 4 (Pn B) followed by ring-opening metathesis polymerization (ROMP) of Pcs AB 3 and B 4 produced asymmetric Pc-appended polymers. Acidic cleavage of the resulting polymers afforded 2,3,9,10,16,17-hexa-(4-methoxyphenoxy)-23-hydroxy Pc 9. A more soluble 2,3,9,10,16,17-hexa-4-pentylphenoxy-23-hydroxy Pc 13 was synthesized by the same strategy and modified with sebacoyl chloride demonstrating that the unmasked hydroxyl site is reactive as a nucleophile.

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U2 - 10.1021/ol900352f

DO - 10.1021/ol900352f

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JO - Organic Letters

JF - Organic Letters

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Asymmetric phthalocyanine synthesi by ROMP-capture-release

Abstract

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