Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 29, Pages 10155-10167Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600897
Keywords
alkynes; arynes; fluorescence; luminescence; tetracyanobutadiene; two-photon absorption
Categories
Funding
- CNRS
- Region Bretagne (ARED)
- Erasmus program
- UR1
- Region Bretagne
- NCN Maestro grant [DEC-2013/10A/ST4/00114]
- Australian Research Council
- Wroclaw Centre for Networking and Supercomputing
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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).
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