Bent and Twisted: Synthesis of an Alkoxy-Substituted (1,5)Naphthalene-paracyclophanediene

Arielle Mann, Matthew D. Hannigan, Bianca L. Dumlao, Chunhua T. Hu, Marcus Weck

Research output: Contribution to journalArticlepeer-review


This contribution describes the synthesis of [2.2](1,5)naphthalenoparacyclophane-1,13-diene in four steps from 1,5-bis(bromomethyl)naphthalene and 1,4-benzenedimethanethiol. Consisting of 2,6-dioctyloxynaphthalene and benzene moieties, the effects of differing arene size on the structure, strain energy, and chemical reactivity of the cyclophanediene are examined. Despite a strain energy of 24.3 kcal/mol, the naphthalenoparacyclophanediene was unreactive toward a library of olefin metathesis catalysts. This diminished reactivity can be explained by the steric hindrance of the twisted olefin. Incorporation of an electron donor (naphthalene) into the rigid paracyclophanediene structure can allow for applications in optoelectronics, chiral ligands, and planar chiral materials.

Original languageEnglish (US)
Pages (from-to)12971-12977
Number of pages7
JournalJournal of Organic Chemistry
Issue number18
StatePublished - Sep 15 2023

ASJC Scopus subject areas

  • Organic Chemistry


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