117396 20220908120609.0 doi 10.1039/d1ma00415h sideral 127232 ART-2021-127232 eng Gámez-Valenzuela S. V-shaped pyranylidene/triphenylamine-based chromophores with enhanced photophysical, electrochemical and nonlinear optical properties 2021 Access copy available to the general public Unrestricted We report the synthesis and comprehensive study of two chromophores based on 4H-pyranylidene moiety as a part of the p-conjugated spacer. Triphenylamine (TPA) acts as donor and tricarbonitrile-based electron-accepting groups complete these V-shaped D-A-D architectures (A, acceptor; D, donor). Their electrochemical, photophysical and nonlinear optical properties are analyzed in detail by using a joint experimental and theoretical approach. The two chromophores exhibit near-infrared fluorescence, large Stokes shift, enhanced emission in tetrahydrofuran/water mixtures and good photostability. Additionally, the dimerization of triphenylamine groups to tetraphenylbenzidine (TPB) takes place upon electrochemical and chemical oxidation showing their peculiar electrochemical behavior and film formation capabilities. Interestingly, high molecular first hyperpolarizabilities and two-photon absorption cross-sections were found, highlighting their potential applications in electro-optical devices. Overall, our work demonstrates that these near-infrared (NIR) fluorescent chromophores are versatile materials with a myriad of applications ranging from optoelectronics to biological applications. © 2021 The Royal Society of Chemistry. info:eu-repo/grantAgreement/ES/DGA/E47-20R info:eu-repo/grantAgreement/ES/ISCIII/RD12-0006-0012 info:eu-repo/grantAgreement/ES/MICINN/PID2019-104293GB-I00 info:eu-repo/grantAgreement/ES/MICINN/PID2019-104307GB-I00-AEI-10.13039-501100011033 info:eu-repo/grantAgreement/ES/MICINN/PID2019-110305GB-I00 info:eu-repo/grantAgreement/ES/MICINN/RTI2018-095410-B-I00 info:eu-repo/semantics/openAccess by-nc http://creativecommons.org/licenses/by-nc/3.0/es/ 0.667 2021 Materials Science (miscellaneous) 2021 Q2 Chemistry (miscellaneous) 2021 Q2 2.0 2021 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Neusser D. Benitez-Martin C. Najera F. Guadix J.A. Moreno-Yruela C. Villacampa B. Universidad de Zaragoza (orcid)0000-0001-9814-0834 Ponce Ortiz R. Ludwigs S. Andreu R. Ruiz Delgado M.C. 2003 395 Universidad de Zaragoza Dpto. Física Materia Condensa. Área Física Materia Condensada 2, 13 (2021), 4255-4263 Mater. adv. Materials Advances 2633-5409 5362964 http://zaguan.unizar.es/record/117396/files/texto_completo.pdf Versión publicada 3345865 http://zaguan.unizar.es/record/117396/files/texto_completo.jpg?subformat=icon icon Versión publicada oai:zaguan.unizar.es:117396 articulos driver 2022-09-08-11:58:34 ARTICLE