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Engineering coumarin-BODIPY thin-films and molecular crystals: Tailoring supramolecular self-assembly for organic electronic applications

Year: 2021

Journal: J. Mol. Struct., Volume 1239, SEP 5

Authors: Ordonez-Hernandez, Javier; Arcos-Ramos, Rafael; Alvarez-Venicio, Violeta; Basiuk, Vladimir A.; Gonzalez-Antonio, Oscar; Flores-Alamo, Marcos; Garcia-Ortega, Hector; Farfan, Norberto; Carreon-Castro, Maria del Pilar

Organizations: DGAPA-UNAM [PAPIIT IN-207421]; CONACYT [411-2016, A1-S7642]; Faculty of Chemistry-UNAM [PAPIIT IN-222819, PAIP 500 0-9056]

Keywords: Coumarin; BODIPYs; Self-assembly; Supramolecular building blocks; Ordered thin-films; Organic semiconductors

Chromophoric coumarin-BODIPY derivatives bridged by an ethynyl pi-bridge were investigated as supramolecular building blocks of organic semiconducting solids through X-ray analysis, UV/V is and fluorescence measurements, and quantum chemical calculations of the frontier orbital energy depending on the chemical environment. Based on a push-pull architecture, the molecular properties of 7-(diethylamino)coumarin core end-capped with BODIPYs as well as the supramolecular self-assembly can be directed through the modification of the ethyny-aryl pi-bridge and the intermolecular interactions it generates. Frontier orbital energy changes depending on chemical environment were performed, in particular, upon adsorption on a flat semiconducting surface. Coumarin-BODIPY building-blocks self-assemble into molecular crystals and highly-ordered thin-films with desirable periodic pi-stacking interactions for semiconducting applications. The present work represents a convenient alternative to engineer organic semiconducting solids based on coumarin-BODIPY systems for organic electronics. (C) 2021 Elsevier B.V. All rights reserved.