New 2, 5-aromatic disubstituted pyrroles, prepared using diazonium salts procedures

• Published in: Journal of molecular structure Vol. 1233; p. 130107
• Main Authors: Vázquez-Hernández, Giovanna Angélica, Delgado-Cruz, Roxana, Sánchez-Vergara, María-Elena, Fomina, Lioudmila, Gómez-Vidales, Virginia, de la Mora, Beatriz, Acosta, Alonso, Ríos, Citlalli, Salcedo, Roberto
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05-06-2021
• Subjects: Diazonium salts; Ferrocene; Fullerene; Organic semiconductor; Fullerene; Diazonium salts; Organic semiconductor; Ferrocene
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2021.130107

•Diazonium salts reactions have been employed to prepare derivatives of fullerene and ferrocene.•The fullerene derivative shows strong semiconductor behavior.•The ferrocene derivative has two isomers, one of them is paramagnetic.
In this work, we have prepared new derivatives of the 2, 5 -aromatic disubstituted pyrrole. Fullerene and ferrocene were used as substituent fragments. These compounds are chemically different, however all of them withdraw electronic charge from the aromatic ring in which they are supported; as a result all the derivatives exhibit semiconductor behaviour. We describe the preparation of these species, and also characterize all of the new compounds. DFT calculations were carried out in order to establish the source of electronic behaviour and to make comparisons between the experimental results. The Kubelka-Munk method indicates that the fullerene compound is a low band gap semiconductor, thus we used this material to prepare thin films. The films were characterized and their optoelectronic behaviour was evaluated.