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Polymers 2018, 10(2), 215; https://doi.org/10.3390/polym10020215

Advantageous Microwave-Assisted Suzuki Polycondensation for the Synthesis of Aniline-Fluorene Alternate Copolymers as Molecular Model with Solvent Sensing Properties

1
Instituto de Biología Molecular y Celular, Universidad Miguel Hernández, E-03202 Elche, Spain
2
Departamento de Química Inorgánica, Orgánica and Bioquímica, Facultad Ciencias y Tecnologías Químicas, Universidad Castilla La Mancha, E-13071 Ciudad Real, Spain
3
Instituto Regional de Investigación Científica Aplicada (IRICA), Edificio Marie Curie, Universidad Castilla La Mancha, E-13071 Ciudad Real, Spain
*
Author to whom correspondence should be addressed.
Received: 18 December 2017 / Revised: 18 February 2018 / Accepted: 20 February 2018 / Published: 22 February 2018
(This article belongs to the Special Issue Tailored Polymer Synthesis by Advanced Polymerization Techniques)
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Abstract

Polymerization via Suzuki coupling under microwave (µW) irradiation has been studied for the synthesis of poly{1,4-(2/3-aminobenzene)-alt-2,7-(9,9-dihexylfluorene)} (PAF), chosen as molecular model. Briefly, µW-assisted procedures accelerated by two orders of magnitude the time required when using classical polymerization processes, and the production yield was increased (>95%). In contrast, although the sizes of the polymers that were obtained by non-conventional heating reactions were reproducible and adequate for most applications, with this methodology the molecular weight of final polymers were not increased with respect to conventional heating. Asymmetric orientation of the amine group within the monomer and the assignments of each dyad or regioregularity, whose values ranged from 38% to 95% with this molecule, were analysed using common NMR spectroscopic data. Additionally, the synthesis of a new cationic polyelectrolyte, poly{1,4-(2/3-aminobenzene)-co-alt-2,7-[9,9´-bis(6’’-N,N,N-trimethylammonium-hexyl)fluorene]} dibromide (PAFAm), from poly{1,4-(2/3-aminobenzene)-co-alt-2,7-[9,9´-bis(6’’-bromohexyl)fluorene]} (PAFBr) by using previously optimized conditions for µW-assisted heating procedures was reported. Finally, the characterization of the final products from these batches showed unkown interesting solvatochromic properties of the PAF molecule. The study of the solvatochromism phenomena, which was investigated as a function of the polarity of the solvents, showed a well-defined Lippert correlation, indicating that the emission shift observed in PAF might be due to its interaction with surrounding environment. Proven high sensitivity to changes of its environment makes PAF a promising candidate of sensing applications. View Full-Text
Keywords: microwave-assisted; suzuki coupling; poly(fluorene-aniline); solvatochromic effect microwave-assisted; suzuki coupling; poly(fluorene-aniline); solvatochromic effect
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Vázquez-Guilló, R.; Falco, A.; Martínez-Tomé, M.J.; Mateo, C.R.; Herrero, M.A.; Vázquez, E.; Mallavia, R. Advantageous Microwave-Assisted Suzuki Polycondensation for the Synthesis of Aniline-Fluorene Alternate Copolymers as Molecular Model with Solvent Sensing Properties. Polymers 2018, 10, 215.

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