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.
All Science Journal Classification (ASJC) codes
- Organic Chemistry