A theoretical study of the effects produced by N-hydroxyalkyl substitution in pyrrole oligomers

This work reports a quantum mechanical investigation of the effects produced by the N-hydroxyalkyl substitution on the molecular and electronic structure of pyrrole-containing oligomers. First, the molecular geometry, torsional potential, ionization potential and π–π * transition energy predicted fo...

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Bibliographic Details
Published in:Synthetic metals 2005-08, Vol.151 (3), p.239-245
Main Authors: Casanovas, Jordi, Cho, Liu Yao, Ocampo, Cintia, Alemán, Carlos
Format: Article
Language:English
Subjects:
Applied sciences
Bipyrrole
Electrical, magnetic and optical properties
Exact sciences and technology
Hydroxyalkyl substitution
N-substitution
Organic polymers
Physicochemistry of polymers
Polypyrrole
Properties and characterization
Quantum mechanical calculations
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Summary:This work reports a quantum mechanical investigation of the effects produced by the N-hydroxyalkyl substitution on the molecular and electronic structure of pyrrole-containing oligomers. First, the molecular geometry, torsional potential, ionization potential and π–π * transition energy predicted for N, N′-dihydroxymethyl-2,2′-bipyrrole and N, N′-dihydroxypropyl-2,2′-bipyrrole have been compared with those obtained for 2,2′-bipyrrole and N, N′-dimethyl-2,2′-bipyrrole. After this, the properties of pyrrole and N-hydroxymethylpyrrole-containing oligomers formed by n repeating units, where n ranges from 1 to 5, have been examined. Results are explained as a combined actuation of electron donation effects induced by the hydroxyl groups, repulsive steric interactions generated by the N-substitution and attractive specific interactions associated to the hydroxyl groups.
ISSN:0379-6779
1879-3290
DOI:10.1016/j.synthmet.2005.05.002