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Pokladek Z, Ripoche N, Betou M, et al. Linear Optical and Third-Order Nonlinear Optical Properties of Some Fluorenyl- and Triarylamine-Containing Tetracyanobutadiene Derivatives. Chemistry. 2016;22(29):10155-67doi: 10.1002/chem.201600897.
Pokladek, Z., Ripoche, N., Betou, M., Trolez, Y., Mongin, O., Olesiak-Banska, J., Matczyszyn, K., Samoc, M., Humphrey, M. G., Blanchard-Desce, M., & Paul, F. (2016). Linear Optical and Third-Order Nonlinear Optical Properties of Some Fluorenyl- and Triarylamine-Containing Tetracyanobutadiene Derivatives. Chemistry (Weinheim an der Bergstrasse, Germany), 22(29), 10155-67. https://doi.org/10.1002/chem.201600897
Pokladek, Ziemowit, et al. "Linear Optical and Third-Order Nonlinear Optical Properties of Some Fluorenyl- and Triarylamine-Containing Tetracyanobutadiene Derivatives." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,29 (2016): 10155-67. doi: https://doi.org/10.1002/chem.201600897
Pokladek Z, Ripoche N, Betou M, Trolez Y, Mongin O, Olesiak-Banska J, Matczyszyn K, Samoc M, Humphrey MG, Blanchard-Desce M, Paul F. Linear Optical and Third-Order Nonlinear Optical Properties of Some Fluorenyl- and Triarylamine-Containing Tetracyanobutadiene Derivatives. Chemistry. 2016 Jul 11;22(29):10155-67. doi: 10.1002/chem.201600897. Epub 2016 Jun 14. PMID: 27297358.
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Chemistry. 2016 Jul 11;22(29):10155-67. doi: 10.1002/chem.201600897. Epub 2016 Jun 14.

Linear Optical and Third-Order Nonlinear Optical Properties of Some Fluorenyl- and Triarylamine-Containing Tetracyanobutadiene Derivatives.

Chemistry (Weinheim an der Bergstrasse, Germany)

Ziemowit Pokladek, Nicolas Ripoche, Marie Betou, Yann Trolez, Olivier Mongin, Joanna Olesiak-Banska, Katarzyna Matczyszyn, Marek Samoc, Mark G Humphrey, Mireille Blanchard-Desce, Frédéric Paul

Affiliations

  1. Faculty of Chemistry, Wroclaw University of Science and Technology, 50-370, Wroclaw, Polen.
  2. Institut des Sciences Chimiques de Rennes, CNRS (UMR 6226), Université de Rennes?1, Campus de Beaulieu, 35042, Rennes Cedex, France.
  3. Research School of Chemistry, Australian National University, Canberra, ACT 2601, Australia.
  4. Ecole Nationale Supérieure de Chimie de Rennes, CNRS (UMR 6226), Institut des Sciences Chimiques de Rennes, 11?allée de Beaulieu, CS 50837, 35708, Rennes Cedex 7, France.
  5. Faculty of Chemistry, Wroclaw University of Science and Technology, 50-370, Wroclaw, Polen. [email protected].
  6. ISM, CNRS (UMR 5255), Université Bordeaux, 33400, Talence, France.
  7. Institut des Sciences Chimiques de Rennes, CNRS (UMR 6226), Université de Rennes?1, Campus de Beaulieu, 35042, Rennes Cedex, France. [email protected].

PMID: 27297358 DOI: 10.1002/chem.201600897

Abstract

The synthesis and characterization of four new tetracyanobutadiene (TCBD) derivatives (1-3 and 2') incorporating 2- or 2,7-fluorenyl and diphenylamino moieties are reported. The electroactivity of 1-3 and 2' was studied by cyclic voltammetry (CV), while the linear optical and (third-order) nonlinear optical (NLO) properties were investigated by electronic spectroscopy and Z-scan studies, respectively. All experimental investigations were rationalized by DFT computations, providing an insight into the electronic structure of these derivatives and on their application potential. We show that these derivatives are nonluminescent in solution at ambient temperatures, but become fluorescent in solvent glasses. This finding constitutes an unprecedented observation for TCBD derivatives. Also, we show by Z-scan studies that these derivatives behave as two-photon absorbers in the near-IR range (800-1050 nm). These third-order NLO properties are discussed and compared with those of their alkynyl precursors (4-6), which have been investigated by two-photon excited fluorescence (TPEF).

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: alkynes; arynes; fluorescence; luminescence; tetracyanobutadiene; two-photon absorption

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