Photophysical Analysis of Aggregation‐Induced Emission (AIE) Luminogens Based on Triphenylamine and Thiophene: Insights into Emission Behavior in Solution and PMMA Films

Author:

Segura Camilo1ORCID,Ormazabal‐Toledo Rodrigo2,García‐Beltrán Olimpo34,Squeo Benedetta M.5,Bachmann Cristian6,Flores Catalina6,Osorio‐Román Igor O.6

Affiliation:

1. Departamento de Química, Facultad de Ciencias Universidad de Chile Las Palmeras 3425 Ñuñoa Región Metropolitana Chile

2. Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmaceúticas Universidad de Chile Dr. Carlos Lorca Tobar 964 Independencia Región Metropolitana Chile

3. Facultad de Ciencias Naturales y Matemáticas Universidad de Ibagué Carrera 22 Calle 67 Ibagué Colombia

4. Centro Integrativo de Biología y Química Aplicada (CIBQA) Universidad Bernardo O'Higgins General Gana 1702 Santiago Región Metropolitana Chile

5. Istituto di Scienze e Tecnologie Chimiche (SCITEC) Consiglio Nazionale delle Ricerche (CNR) Via A. Corti 20133 Milano Italy

6. Instituto de Ciencias Químicas, Facultad de Ciencias Universidad Austral de Chile Av. Rector Eduardo Morales 33 Valdivia 509000 Chile

Abstract

AbstractAggregation‐Induced Emission (AIE) luminogens have garnered significant interest due to their distinctive applications in different applications. Among the diverse molecular architectures, those based on triphenylamine and thiophene hold prominence. However, a comprehensive understanding of the deactivation mechanism both in solution and films remains lacking. In this study, we synthesized and characterized spectroscopically two AIE luminogens: 5‐(4‐(bis(4‐methoxyphenyl)amino)phenyl)thiophene‐2‐carbaldehyde (TTY) and 5′‐(4‐(bis(4‐methoxyphenyl)amino)phenyl)‐[2,2′‐bithiophene]‐5‐carbaldehyde (TTO). Photophysical and theoretical analyses were conducted in both solution and PMMA films to understand the deactivation mechanism of TTY and TTO. In diluted solutions, the emission behavior of TTY and TTO is influenced by the solvent, and the deactivation of the excited state can occur via locally excited (LE) or twisted intramolecular charge transfer (TICT) state. In PMMA films, rotational and translational movements are constrained, necessitating emission solely from the LE state. Nevertheless, in the PMMA film, excimers‐like structures form, resulting in the emergence of a longer wavelength band and a reduction in emission intensity. The zenith of emission intensity occurs when molecules are dispersed at higher concentrations within PMMA, effectively diminishing the likelihood of excimer‐like formations. Luminescent Solar Concentrators (LSC) were fabricated to validate these findings, and the optical efficiency was studied at varying concentrations of luminogen and PMMA.

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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