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Intramolecular Hydrogen‐Bond‐Assisted Planarization of Asymmetrically Functionalized Alternating Phenylene–Pyridinylene Copolymers
Author(s) -
Vetrichelvan Muthalagu,
Valiyaveettil Suresh
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500078
Subject(s) - polymer , hydrogen bond , gel permeation chromatography , thermogravimetric analysis , materials science , polymer chemistry , intramolecular force , pyridine , phenylene , chemistry , photochemistry , organic chemistry , molecule
Abstract We report on the synthesis and characterization of a series of asymmetrically functionalized amphiphilic polymers with alternating π‐donor units (e.g., substituted benzene) and π‐acceptor units (e.g., pyridine) along the polymer backbone. The purpose of our present work involves incorporation of functional groups along the main chain to form intrachain hydrogen bonds, which promote planarization of the polymer backbone, and to fine‐tune the optical properties. The structure–property relationship of polymers P 1 – P 6 was investigated by means of analytical methods, such as FTIR spectroscopy, 1 H and 13 C NMR spectroscopy, UV/Vis spectroscopy, fluorescence spectroscopy, gel permeation chromatography, thermogravimetric analysis, cyclic voltammetry, and X‐ray powder diffraction. All polymers were soluble in common organic solvents, and the optical and fluorescence spectra of the polymers showed significant changes according to the formation ( P 4 , P 5 ) or absence ( P 6 ) of intramolecular hydrogen bonding along the polymer backbone. Moreover, the 2,6‐ or 3,5‐linkage of the pyridine rings in P 5 and P 6 , respectively, reduced the conjugation along the polymer backbone and this is reflected in their optical properties. The optical properties of the polymers were influenced by the addition of acid ( P 1 – P 6 ), base ( P 4 – P 6 ), and metal ions (e.g., Cu 2+ , Fe 3+ , Ag + , Ni 2+ , Pd 2+ , Mn 2+ , Zn 2+ , Mg 2+ , and Pr 3+ ). Such polymers could be used in various applications, including sensors and stimuli‐responsive displays.