Benzodifuroxazinones, a new class of heteroacene molecules for possible applications in organic electronics: Synthesis, electronic properties and crystal structure

Antonio Carella, Fabio Borbone, Antonio Roviello, Giuseppina Roviello, Angela Tuzi, Alexey Kravinsky, Rafi Shikler, Giovanni Cantele, Domenico Ninno

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

A novel class of heteroacene molecules, benzodifuroxazin-4-ones, has been effectively synthesized by means of a thermally activated double cyclization reaction starting from amidic precursors. The new molecules were thermally and optically characterized, revealing an outstanding thermal stability to oxidation and an uncommon enhancement of fluorescent properties in solid state as compared to solution. As shown by single-crystal XRD analysis, the molecules crystallize in a face-to-face (π-stack) arrangement instead of the herringbone structure typical of the most acene derivatives. The electronic properties of both molecules and crystals have been investigated by means of a detailed Density Functional Theory computational analysis: very stable HOMO energies have been calculated and, from the band structure analysis, it is possible to suggest a preferential direction of charge transport along the π-stacking direction. All the reported properties indicate this new class of heteroacene derivatives as interesting candidates for a possible application in organic electronics.

Original languageEnglish
Pages (from-to)116-125
Number of pages10
JournalDyes and Pigments
Volume95
Issue number1
DOIs
StatePublished - 1 Oct 2012

Keywords

  • Crystal structure determination
  • Density functional calc.
  • Heteroacenes
  • Organic electronics
  • Solid phase synthesis
  • Solid state fluorescence

ASJC Scopus subject areas

  • Chemical Engineering (all)
  • Process Chemistry and Technology

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