Health & Environmental Research Online (HERO)


Print Feedback Export to File
3453253 
Journal Article 
Pentaleno[1,2-a:4,5']diacenaphthylenes: Uniquely Stabilized Pentalene Derivatives 
Yuan, B; Zhuang, J; Kirmess, KM; Bridgmohan, CN; Whalley, AC; Wang, L; Plunkett, KN 
2016 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
81 
18 
8312-8318 
English 
27559925 
WOS:000383639500020 
We demonstrate the preparation of diacenaphthopentalene derivatives via a palladium-catalyzed dimerization of 1-iodo-2-arylethynyl-acenaphthylenes. The resulting 7,14-diarylpentaleno[1,2-a:4,5a']diacenaphthylenes, which contain four linearly fused five-membered rings, are benchtop stable and behave as hole-transporting or ambipolar semiconductors in organic field effect transistors. The X-ray crystal structure shows the important role of the fused naphthalene unit that enforces a formal pentalene subunit at the central five-membered rings and [5]-radialene-like structures at the proximal five-membered rings. Nucleus-independent chemical shift (NICS) calculations show the internal pentalene rings are intermediate in antiaromaticity character between known pentalene and dibenzopentalenes derivatives. The diacenaphthopentalene derivatives give high optical gap materials owing to a forbidden HOMO to LUMO transition, yet have narrow electrochemical gaps and are reduced at small negative potentials giving LUMO energy levels of -3.57 to -3.74 eV.