TY - JOUR
T1 - Synthesis and morphological characterization of a new conjugated polymer based on benzobisoxazole and thiophene systems
AU - Ahumada, Juan Carlos
AU - Leyton, Patricio
AU - Aristizabal, Juliet Andrea
AU - Soto, Juan Pablo
N1 - Funding Information:
The authors acknowledge financial support from Pontificia Universidad Cat?lica de Valpara?so, DII Grant No. 039.340/2016 and are also grateful to CONICYT-FONDEQUIP program NMR 300, Grant No. EQM 130154, and FONDECYT Grant No. 1140810, ECOS-CONICYT Grant No. C14E05 and CONICYT?Beca Doctorado Nacional No. 21140238.
Funding Information:
Acknowledgements The authors acknowledge financial support from Pontificia Universidad Católica de Valparaíso, DII Grant No. 039.340/2016 and are also grateful to CONICYT-FONDEQUIP program NMR 300, Grant No. EQM 130154, and FONDECYT Grant No. 1140810, ECOS-CONICYT Grant No. C14E05 and CONICYT—Beca Doctorado Nacional No. 21140238.
Publisher Copyright:
© 2017, Springer-Verlag Berlin Heidelberg.
PY - 2018/2/1
Y1 - 2018/2/1
N2 - In the present work, the synthesis, electropolymerization and polymer characterization of 2,6-di(4-butylphenyl)-4,8-dithiophenylbenzobisoxazole are reported. The synthesis involves several steps from 1,4-benzoquinone to form 2,5-diamine-3,6-dibromohydroquinone, which is condensed with 4-butylbenzoyl chloride and later with thiophen-2-ylmagnesium bromide through Kumada coupling reactions. This monomer is polymerized by potentiodynamic cyclic voltammetry. The voltammograms show a dependency on the range of applied potential, and three different processes of thermodynamically reversible oxidation and reduction occur on a platinum surface. Theoretical calculations are used to characterize these redox processes. The distribution of the frontier orbital density for the monomer and trimer forms show the participation of the thiophene ring in the polymerization processes and partial oxidation of the benzoxazole fragment. The characterization of the polymeric deposit was carried out by scanning electron microscopy and Raman spectroscopy. A dependence of both the morphology and vibrational state of the polymer on the potential range applied exists. This is attributed to the different conformations and dihedral angles of the macromolecule. Finally, the optical properties of the material indicate the existence of intramolecular charge transfer through the system’s thiophene and benzobisoxazole (donor and acceptor).
AB - In the present work, the synthesis, electropolymerization and polymer characterization of 2,6-di(4-butylphenyl)-4,8-dithiophenylbenzobisoxazole are reported. The synthesis involves several steps from 1,4-benzoquinone to form 2,5-diamine-3,6-dibromohydroquinone, which is condensed with 4-butylbenzoyl chloride and later with thiophen-2-ylmagnesium bromide through Kumada coupling reactions. This monomer is polymerized by potentiodynamic cyclic voltammetry. The voltammograms show a dependency on the range of applied potential, and three different processes of thermodynamically reversible oxidation and reduction occur on a platinum surface. Theoretical calculations are used to characterize these redox processes. The distribution of the frontier orbital density for the monomer and trimer forms show the participation of the thiophene ring in the polymerization processes and partial oxidation of the benzoxazole fragment. The characterization of the polymeric deposit was carried out by scanning electron microscopy and Raman spectroscopy. A dependence of both the morphology and vibrational state of the polymer on the potential range applied exists. This is attributed to the different conformations and dihedral angles of the macromolecule. Finally, the optical properties of the material indicate the existence of intramolecular charge transfer through the system’s thiophene and benzobisoxazole (donor and acceptor).
KW - Benzobisoxazole
KW - Conducting polymer
KW - Electropolymerization
KW - Polybenzobisoxazole
KW - Polythiophene
UR - http://www.scopus.com/inward/record.url?scp=85019070509&partnerID=8YFLogxK
U2 - 10.1007/s00289-017-2057-4
DO - 10.1007/s00289-017-2057-4
M3 - Article
AN - SCOPUS:85019070509
VL - 75
SP - 597
EP - 610
JO - Polymer Bulletin
JF - Polymer Bulletin
SN - 0170-0839
IS - 2
ER -