Giulia Neri1, Enza Fazio2, Antonia Nostro1, Placido Giuseppe Mineo3, Angela Scala1, Antonio Rescifina4, Anna Piperno1. 1. Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, V.le F. Stagno d'Alcontres 31, 98166 Messina, Italy. 2. Department of Mathematical and Computational Sciences, Physics Science and Earth Science, University of Messina, V.le F. Stagno d'Alcontres 31, I-98166 Messina, Italy. 3. Department of Chemical Sciences, University of Catania, V.le A. Doria, 95125 Catania, Italy. 4. Department of Drug and Health Sciences, University of Catania, V.le A. Doria, 95125 Catania, Italy.
Abstract
Münchnones are mesoionic oxazolium 5-oxides with azomethine ylide characteristics that provide pyrrole derivatives by a 1,3-dipolar cycloaddition (1,3-DC) reaction with acetylenic dipolarophiles. Their reactivity was widely exploited for the synthesis of small molecules, but it was not yet investigated for the functionalization of graphene-based materials. Herein, we report our results on the preparation of münchnone functionalized graphene via cycloaddition reactions, followed by the spontaneous loss of carbon dioxide and its further chemical modification to silver/nisin nanocomposites to confer biological properties. A direct functionalization of graphite flakes into few-layers graphene decorated with pyrrole rings on the layer edge was achieved. The success of functionalization was confirmed by micro-Raman and X-ray photoelectron spectroscopies, scanning transmission electron microscopy, and thermogravimetric analysis. The 1,3-DC reactions of münchnone dipole with graphene have been investigated using density functional theory to model graphene. Finally, we explored the reactivity and the processability of münchnone functionalized graphene to produce enriched nano biomaterials endowed with antimicrobial properties.
Münchnones are mesoionic oxazolium 5-oxides with n class="Chemical">azomethine ylide characteristics that provide pyrrole derivatives by a 1,3-dipolar cycloaddition (1,3-DC) reaction with acetylenic dipolarophiles. Their reactivity was widely exploited for the synthesis of small molecules, but it was not yet investigated for the functionalization of graphene-based materials. Herein, we report our results on the preparation of münchnone functionalized graphene via cycloaddition reactions, followed by the spontaneous loss of carbon dioxide and its further chemical modification to silver/nisin nanocomposites to confer biological properties. A direct functionalization of graphite flakes into few-layers graphene decorated with pyrrole rings on the layer edge was achieved. The success of functionalization was confirmed by micro-Raman and X-ray photoelectron spectroscopies, scanning transmission electron microscopy, and thermogravimetric analysis. The 1,3-DC reactions of münchnone dipole with graphene have been investigated using density functional theory to model graphene. Finally, we explored the reactivity and the processability of münchnone functionalized graphene to produce enriched nano biomaterials endowed with antimicrobial properties.
Entities:
Keywords:
1,3-dipolar cycloaddition; antibacterial graphene; graphene density functional theory (DFT) calculation; mesoionic compounds; münchnone; nisin; oxazolone; reduced graphene; silver nanoparticles
Authors: Helena Uceta; María Vizuete; José R Carrillo; Myriam Barrejón; José Luis G Fierro; Maria Pilar Prieto; Fernando Langa Journal: Chemistry Date: 2019-10-17 Impact factor: 5.236
Authors: Rosendo Valero; Ramon Costa; Ibério de P R Moreira; Donald G Truhlar; Francesc Illas Journal: J Chem Phys Date: 2008-03-21 Impact factor: 3.488
Authors: Petr Lazar; František Karlický; Petr Jurečka; Mikuláš Kocman; Eva Otyepková; Klára Šafářová; Michal Otyepka Journal: J Am Chem Soc Date: 2013-04-16 Impact factor: 15.419
Authors: André Abts; Antonino Mavaro; Jan Stindt; Patrick J Bakkes; Sabine Metzger; Arnold J M Driessen; Sander H J Smits; Lutz Schmitt Journal: Int J Pept Date: 2011-09-18