%0 Journal Article %T Linear Optical and Third-Order Nonlinear Optical Properties of Some Fluorenyl- and Triarylamine-Containing Tetracyanobutadiene Derivatives %+ Institute of Physical and Theoretical Chemistry %+ Institut des Sciences Chimiques de Rennes (ISCR) %+ Australian National University (ANU) %+ Institut des Sciences Moléculaires (ISM) %A Pokladek, Ziemowit %A Ripoche, Nicolas %A Betou, Marie %A Trolez, Yann %A Mongin, Olivier %A Olesiak-Banska, Joanna %A Matczyszyn, Katarzyna %A Samoc, Marek %A Humphrey, Mark G. %A Blanchard-Desce, Mireille %A Paul, Frédéric %Z CNRS %Z "Region Bretagne" (ARED) %Z Erasmus program %Z UR1 %Z Region Bretagne %Z NCN Maestro grant [DEC-2013/10A/ST4/00114] %Z Australian Research Council %Z Wroclaw Centre for Networking and Supercomputing %< avec comité de lecture %@ 0947-6539 %J Chemistry - A European Journal %I Wiley-VCH Verlag %V 22 %N 29 %P 10155--10167 %8 2016 %D 2016 %R 10.1002/chem.201600897 %M 27297358 %K density-functional theory %K photoinduced electron-transfer %K excitation cross-sections %K 2-photon absorption %K organic nanodots %K chromophores %K fluorescence %K complexes %K molecules %K dyes %Z Chemical Sciences %Z Chemical Sciences/Material chemistryJournal articles %X 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). %G English %2 https://univ-rennes.hal.science/hal-01357408/document %2 https://univ-rennes.hal.science/hal-01357408/file/Hal_Version.pdf %2 https://univ-rennes.hal.science/hal-01357408/file/Hal_ESI.pdf %L hal-01357408 %U https://univ-rennes.hal.science/hal-01357408 %~ UNIV-RENNES1 %~ CNRS %~ INSA-RENNES %~ ENSC-RENNES %~ UNIV-BORDEAUX %~ ISCR %~ SCR_OMC2012 %~ SCR_CPM %~ SCR-COS %~ STATS-UR1 %~ UR1-SPM %~ INC-CNRS %~ UR1-UFR-SPM %~ UR1-HAL %~ ISCR-CORINT %~ UR1-SDLM %~ TEST-UNIV-RENNES %~ TEST-UR-CSS %~ UNIV-RENNES %~ INSA-GROUPE %~ ISCR-CORINT1 %~ UR1-MMS %~ ISCR-CORINT3 %~ TEST2-HALCNRS %~ TEST3-HALCNRS