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

doi:10.1002/chem.201101198

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

Research output: Contribution to journal › Article › peer-review

44 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 language	English (US)
Pages (from-to)	10312-10322
Number of pages	11
Journal	Chemistry - A European Journal
Volume	17
Issue number	37
DOIs	https://doi.org/10.1002/chem.201101198
State	Published - Sep 5 2011
Externally published	Yes

Keywords

Raman spectroscopy
density functional theory
hexaazatriphenylenes
supramolecular chemistry

ASJC Scopus subject areas

General Chemistry
Catalysis
Organic Chemistry

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10.1002/chem.201101198

Cite this

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

Juárez, R, Oliva, MM, Ramos, M, Segura, JL, Alemán, C, Rodríguez-Ropero, F, Curcó, D, Montilla, F, Coropceanu, V , Brédas, JL, Qi, Y, Kahn, A, Ruiz Delgado, MC, Casado, J & López Navarrete, JT 2011, 'Hexaazatriphenylene (HAT) versus tri-HAT: The bigger the better?', Chemistry - A European Journal, vol. 17, no. 37, pp. 10312-10322. https://doi.org/10.1002/chem.201101198

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title = "Hexaazatriphenylene (HAT) versus tri-HAT: The bigger the better?",

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.",

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AU - Segura, José L.

AU - Alemán, Carlos

AU - Rodríguez-Ropero, Francisco

AU - Curcó, David

AU - Montilla, Francisco

AU - Coropceanu, Veaceslav

AU - Brédas, Jean Luc

AU - Qi, Yabing

AU - Kahn, Antoine

AU - Ruiz Delgado, M. Carmen

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AB - 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.

KW - Raman spectroscopy

KW - density functional theory

KW - hexaazatriphenylenes

KW - supramolecular chemistry

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

Abstract

Keywords

ASJC Scopus subject areas

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