Synthesis and fluorescence properties of a soluble polypyrrole derivative based on a dipyrrole monomer

• Published in: Synthetic metals Vol. 195; pp. 185 - 192
• Main Authors: Zhang, Shihu, Wang, Guolong, Lv, Guowei, Yu, Demei, Ding, Yucheng
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 01.09.2014; Elsevier
• Subjects: Applied sciences; Doppler effect; Exact sciences and technology; Excitation; Fluorescence; Monomers; Organic polymers; Physicochemistry of polymers; Polymerization; Polymers with particular properties; Polypyrrole derivative; Preparation, kinetics, thermodynamics, mechanism and catalysts; Red shift; Soluble; Solvents; Wavelengths; Fluorescence; Soluble; Polypyrrole derivative; MDPP; PMDPP; Molecular structure; Bifunctional compound; Aromatic polymer; Pyrrole derivative polymer; Experimental study; Functional polymer; Absorption spectrum; Organic solution; Conjugated polymer; Morphology; Preparation; Concentration effect; Carboxamide; Soluble compound; Amorphous polymer; Oxidative polymerization
• ISSN: 0379-6779; 1879-3290
• DOI: 10.1016/j.synthmet.2014.06.006

•A monomer 2-methyl-1,3-di(1H-pyrrol-1-yl)propan-1-one (MDPP) was synthesized.•The soluble polymer of MDPP (PMDPP) was obtained by the chemical polymerization.•The polymerization mechanism of MDPP was discussed.•The fluorescence measurements were carried out on PMDPP solutions. A unique dipyrrole monomer 2-methyl-1,3-di(1H-pyrrol-1-yl)propan-1-one (MDPP) was synthesized and the corresponding branched polymer (PMDPP) with the molecular weight (Mw) of 2416 was obtained by the chemical polymerization. The molecular structures of MDPP and PMDPP were characterized by FTIR and NMR. It was found that the polymerization of MDPP was accomplished on the pyrrole ring which is attached to the carbonyl group. The resulting polymer had an amorphous structure and could be dissolved in many organic solvents. The fluorescence measurements were carried out on PMDPP solutions, which emitted the green light in the range of 556–574nm under the excitation of 467nm depending on the solvents. It is interesting that the Stokes shift of the PMDPP solution was more sensitive to the electron donor–acceptor properties of solvent rather than the polarity of solvent. Notably, the maximum emission wavelength (λmaxem) of the PMDPP solution showed a red shift from 556nm to 586nm with the increase of PMDPP concentration from 1.80×E−5g/ml to 6.314×E−4g/ml in THF, and it exhibited a remarkable dependence on the excitation wavelength in the range of 327–507nm, which led to a gradual red shift of the λmaxem from 510nm to 584nm.