Toward Covalently Linked Organic Networks: Model Studies and Connector Syntheses

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

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)8814-8820
Number of pages7
JournalJournal of Organic Chemistry
Volume62
Issue number25
DOIs
StatePublished - Jan 1 1997

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Feldman, K. S., Campbell, R. F., Saunders, J. C., Ahn, C., & Masters, K. M. (1997). Toward Covalently Linked Organic Networks: Model Studies and Connector Syntheses. Journal of Organic Chemistry, 62(25), 8814-8820. https://doi.org/10.1021/jo9714167