Benzocyclobutenoacenaphthylene Stilbenes. 1. Synthesis and Thermal Properties

• Published in: Journal of organic chemistry Vol. 63; no. 26; pp. 9698 - 9702
• Main Authors: Buchacher, Petra, Helgeson, Roger, Wudl, Fred
• Format: Journal Article
• Language: English
• Published: American Chemical Society 25-12-1998
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo981016z

In this paper the synthesis and characterization of a new class of molecules based on 6b,10b-dihydrobenzo[j]cyclobut[a]acenaphthylene (DBCA) with potentially interesting optical and electronic properties are described. The mentioned compounds contain one or two DBCA units linked via a double bond to an aromatic system. The synthesis of these compounds is mainly carried out by Heck and/or Wittig reactions. The introduction of DBCA units in molecules is interesting in two respects:  (1) It will influence the electronic and optical properties of the compounds, and (2) it will induce dimerization (polymerization) because DBCA can, upon thermolysis or photolysis, be converted into a biradicaloid species (“pleiadene”) which dimerizes. Thus suitable compounds could be used as monomers for photochemically or thermally induced polymerization.