V-shaped pyranylidene/triphenylamine-based chromophores with enhanced photophysical, electrochemical and nonlinear optical properties

Gámez-Valenzuela S. ; Neusser D. ; Benitez-Martin C. ; Najera F. ; Guadix J.A. ; Moreno-Yruela C. ; Villacampa B. (Universidad de Zaragoza) ; Ponce Ortiz R. ; Ludwigs S. ; Andreu R. ; Ruiz Delgado M.C.

Resumen: 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.

Idioma: Inglés

DOI: 10.1039/d1ma00415h

Año: 2021

Publicado en: Materials Advances 2, 13 (2021), 4255-4263
ISSN: 2633-5409

Factor impacto CITESCORE: 2.0 - Materials Science (Q3)

Factor impacto SCIMAGO: 0.667 - Materials Science (miscellaneous) (Q2) - Chemistry (miscellaneous) (Q2)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E47-20R
Financiación: info:eu-repo/grantAgreement/ES/ISCIII/RD12-0006-0012
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2019-104293GB-I00
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2019-104307GB-I00-AEI-10.13039-501100011033
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2019-110305GB-I00
Financiación: info:eu-repo/grantAgreement/ES/MICINN/RTI2018-095410-B-I00

Tipo y forma: Article (Published version)

Área (Departamento): Área Física Materia Condensada (Dpto. Física Materia Condensa.)