Polythiophenes based on pyrene as pendant group: Synthesis, structural characterization and luminescent properties

• Published in: Journal of molecular structure 2016-01, Vol.1103, p.25-34
• Main Authors: González-Juárez, E., Güizado-Rodríguez, M., Barba, V., Melgoza-Ramírez, M., Rodríguez, M., Ramos-Ortíz, G., Maldonado, J.L.
• Format: Article
• Language: English
• Subjects: Luminescence; Optical properties; Polythiophene; Pyrene chromophore
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2015.09.011

Novel polythiophenes (PTs) derived from 3-alkylthiophenes (R = hexyl, octyl) and a thiophene functionalized with pyrene chromophore were synthesized. A homopolymer and copolymers were obtained by using different stoichiometric ratios, and their photophysical properties were investigated. Physicochemically characterized by FT-IR, 1H NMR, UV–vis, DSC-TGA and GPC as well as fluorescence spectroscopy, the new PTs reached moderate molecular weight distributions, exhibited good thermal properties and were easily processable for depositing films of satisfactory optical quality with third-order nonlinear optical susceptibilities of approximately 10–12 esu. The new PTs showed absorption and emission bands ranging from 346 to 430 nm, and from 450 to 570 nm, respectively, with quantum yields between 0.07 and 0.25. In addition, nanoparticles were obtained from the PTs by using the mini-emulsion technique. Their spectroscopic characteristics and morphology were determined by means of UV–vis spectroscopy and SEM analysis. Novel polythiophenes (PTs) derived of alkylthiophenes (R = hexyl, octyl) and a thiophene functionalized with pyrene chromophore were synthesized. A homopolymer and copolymers were obtained by using different stoichiometric ratios, and their photophysical properties were investigated. The new PTs showed absorption and emission bands ranging from 346 to 430 nm, and from 450 to 570 nm, respectively, with quantum yields between 0.07 and 0.25. In addition, nanoparticles were obtained from the PTs by using the mini-emulsion technique. [Display omitted] •PTs derived of 3-alkylthiophenes and thiophene with pyrene were synthesized.•Photophysical properties of PTs with different stoichiometric ratios were studied.•PTs showed absorption and emission bands blue shifted when the pyrene group ratio increase.•Third-order nonlinear optical susceptibilities of some PTs were determined.•Nanoparticles of these PTs using the miniemulsion technique were investigated.