TOWARD COVALENTLY-LINKED ORGANIC NETWORKS - MODEL STUDIES AND CONNECTOR SYNTHESES

A model 1-naphthoic acid bearing a peri-positioned cinnamic acid resid ue crystallizes as a closed H-bonded dimer. Irradiation of this crysta lline solid provides an alpha-truxillate-type cyclobutane photodimer i n quantitative yield, Further synthesis studies have led to more highl y functionalized naphthoic/cinnamic acid species capable of(pseudo)cen trosymmetric attachment to polyvalent hubs, This system demonstrates t he feasibility of designing a covalent molecular connector whose orien tation is encoded by its H-bonding pattern.