Hexaazatriphenylene (HAT) versus tri-HAT: The bigger the better?

Rafael Juárez, María Moreno Oliva, Mar Ramos, José L. Segura, Carlos Alemán, Francisco Rodríguez-Ropero, David Curcó, Francisco Montilla, Veaceslav Coropceanu, Jean Luc Brédas, Yabing Qi, Antoine Kahn, M. Carmen Ruiz Delgado, Juan Casado, Juan T. López Navarrete

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30 Scopus citations

Abstract

A new hexaazatriphenylene (HAT) derivative formed by the fusion of three HAT units has been prepared and its electronic and molecular structures have been fully characterized by optical and vibrational Raman spectroscopy, electrochemistry, solid-state UV and inverse photoemission spectroscopy (UPS and IPES), and by quantum-chemical calculations. A comparative HAT versus tri-HAT study was performed. The fusion of three HAT molecules causes modifications in the optical and electrochemical properties consistent with enhanced π-electron delocalization attained in a bigger planar core. Such combined experimental and theoretical studies are useful to balance chemical design with supramolecular engineering directed to find enhanced characteristics for new organic semiconductor applications.

Original languageEnglish (US)
Pages (from-to)10312-10322
Number of pages11
JournalChemistry - A European Journal
Volume17
Issue number37
DOIs
StatePublished - Sep 5 2011

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Keywords

  • Raman spectroscopy
  • density functional theory
  • hexaazatriphenylenes
  • supramolecular chemistry

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    Juárez, R., Oliva, M. M., Ramos, M., Segura, J. L., Alemán, C., Rodríguez-Ropero, F., Curcó, D., Montilla, F., Coropceanu, V., Brédas, J. L., Qi, Y., Kahn, A., Ruiz Delgado, M. C., Casado, J., & López Navarrete, J. T. (2011). Hexaazatriphenylene (HAT) versus tri-HAT: The bigger the better? Chemistry - A European Journal, 17(37), 10312-10322. https://doi.org/10.1002/chem.201101198