Toward Covalently Linked Organic Networks: Model Studies and Connector Syntheses

Ken S. Feldman; Robert F. Campbell; Joe C. Saunders; Chuljin Ahn; Katherine M. Masters

doi:10.1021/jo9714167

Toward Covalently Linked Organic Networks: Model Studies and Connector Syntheses

Ken S. Feldman, Robert F. Campbell, Joe C. Saunders, Chuljin Ahn, Katherine M. Masters

Chemistry

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

26 Scopus citations

Abstract

A model 1-naphthoic acid bearing a peri-positioned cinnamic acid residue crystallizes as a closed H-bonded dimer. Irradiation of this crystalline solid provides an α-truxillate-type cyclobutane photodimer in quantitative yield. Further synthesis studies have led to more highly functionalized naphthoic/cinnamic acid species capable of (pseudo)centrosymmetric attachment to polyvalent hubs. This system demonstrates the feasibility of designing a covalent molecular connector whose orientation is encoded by its H-bonding pattern.

Original language	English (US)
Pages (from-to)	8814-8820
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	62
Issue number	25
DOIs	https://doi.org/10.1021/jo9714167
State	Published - Jan 1 1997

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo9714167

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abstract = "A model 1-naphthoic acid bearing a peri-positioned cinnamic acid residue crystallizes as a closed H-bonded dimer. Irradiation of this crystalline solid provides an α-truxillate-type cyclobutane photodimer in quantitative yield. Further synthesis studies have led to more highly functionalized naphthoic/cinnamic acid species capable of (pseudo)centrosymmetric attachment to polyvalent hubs. This system demonstrates the feasibility of designing a covalent molecular connector whose orientation is encoded by its H-bonding pattern.",

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AU - Feldman, Ken S.

AU - Campbell, Robert F.

AU - Saunders, Joe C.

AU - Ahn, Chuljin

AU - Masters, Katherine M.

PY - 1997/1/1

Y1 - 1997/1/1

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AB - A model 1-naphthoic acid bearing a peri-positioned cinnamic acid residue crystallizes as a closed H-bonded dimer. Irradiation of this crystalline solid provides an α-truxillate-type cyclobutane photodimer in quantitative yield. Further synthesis studies have led to more highly functionalized naphthoic/cinnamic acid species capable of (pseudo)centrosymmetric attachment to polyvalent hubs. This system demonstrates the feasibility of designing a covalent molecular connector whose orientation is encoded by its H-bonding pattern.

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Toward Covalently Linked Organic Networks: Model Studies and Connector Syntheses

Abstract

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