2026-04-27T01:59:26Zhttps://repisalud.isciii.es/rest/oai/request
oai:repisalud.isciii.es:20.500.12105/183542024-11-28T15:10:28Zcom_20.500.12105_15322com_20.500.12105_2051col_20.500.12105_16927
Repisalud author Gámez-Valenzuela, Sergio author Neusser, David author Benitez-Martín, Carlos author Najera, Francisco author Guadix, Juan A. author Moreno-Yruela, Carlos author Villacampa, Belén author Ponce Ortíz, Rocío author Ludwigs, Sabine author Andreu, Raquel author Ruiz Delgado, M. Carmen authoraffiliation [Gámez-Valenzuela,S; Ponce Ortíz,R; Ruiz Delgado,MC] Department of Physical Chemistry, University of Malaga,, Malaga, Spain. [Neusser,D; Ludwigs,S] IPOC – Functional Polymers, Institute of Polymer Chemistry, University of Stuttgart, Stuttgart, Germany. [Benitez-Martín,C; Najera,F] Departamento de Química Orgánica, Universidad de Málaga-IBIMA, Málaga, Spain. [Benitez-Martín,C; Najera,F; Guadix,JA] Centro Andaluz de Nanomedicina y Biotecnología-BIONAND, Parque Tecnológico de Andalucía, Campanillas, Málaga, Spain. [Guadix,JA] Departamento de Biología Animal, Facultad de Ciencias, Universidad de Málaga-IBIMA, Málaga, Spain. [Moreno-Yruela,C; Andreu,R] Instituto de Nanociencia y Materiales de Aragón (INMA)-Departamento de Química Orgánica, CSIC-Universidad de Zaragoza, Zaragoza, Spain. [Moreno-Yruela,C] Center for Biopharmaceuticals & Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Copenhagen, Denmark. [Villacampa,B] Instituto de Nanociencia y Materiales de Arago´n (INMA)-Departamento de Física de la Materia Condensada, CSIC-Universidad de Zaragoza, Zaragoza, Spain. 2024-02-19T15:28:27Z 2024-02-19T15:28:27Z 2021-05-25 http://hdl.handle.net/10668/4531 http://hdl.handle.net/20.500.12105/18354 10.1039/D1MA00415H 2633-5409 Material Advances We report the synthesis and comprehensive study of two chromophores based on 4H-pyranylidene moiety as a part of the π-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. eng Fluorescence Electrons Dimerization Tetrahydrofuran Chromophore-Assisted Light Inactivation Chemical oxidation Fluorescencia Electrones Dimerización 4-Butirolactona Inactivación por luz asistida por cromóforos Oxidación química V-shaped pyranylidene/triphenylamine-based chromophores with enhanced photophysical, electrochemical and nonlinear optical properties research article