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


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Title:
Advantageous Microwave-Assisted Suzuki Polycondensation for the Synthesis of Aniline-Fluorene Alternate Copolymers as Molecular Model with Solvent Sensing Properties
Authors:
Vázquez Guilló, Rebeca  
Falcó, Alberto  
Martínez Tomé, María José
Mateo , C. Reyes  
Herrero, Maria Antonia  
Vázquez, Ester  
Mallavia, Ricardo  
Editor:
MDPI
Department:
Departamentos de la UMH::Agroquímica y Medio Ambiente
Issue Date:
2018-02-20
URI:
https://hdl.handle.net/11000/30738
Abstract:
Polymerization via Suzuki coupling under microwave ( W) 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, W-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 W-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.
Keywords/Subjects:
microwave-assisted
suzuki coupling
poly(fluorene-aniline)
solvatochromic effect
Knowledge area:
CDU: Ciencias puras y naturales: Química
Type of document:
application/pdf
Access rights:
info:eu-repo/semantics/openAccess
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
DOI:
https://doi.org/10.3390/polym10020215
Appears in Collections:
Artículos Agroquímica y Medio Ambiente



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