Molecular aggregation of naphthalimide organic semiconductors assisted by amphiphilic and lipophilic interactions: a joint theoretical and experimental study

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Title: Molecular aggregation of naphthalimide organic semiconductors assisted by amphiphilic and lipophilic interactions: a joint theoretical and experimental study
Authors: Arrechea-Marcos, Iratxe | Echegaray, Paula de | Mancheño, María José | Ruiz Delgado, María del Carmen | Ramos, María del Mar | Quintana Arévalo, José Antonio | Villalvilla Soria, José Moisés | Díaz-García, María A. | López Navarrete, Juan T. | Ponce Ortiz, Rocío | Segura, José L.
Research Group/s: Física de la Materia Condensada
Center, Department or Service: Universidad de Alicante. Departamento de Física Aplicada | Universidad de Alicante. Instituto Universitario de Materiales
Keywords: Molecular aggregation | Naphthalimide organic semiconductors | Amphiphilic and lipophilic interactions
Knowledge Area: Física Aplicada | Física de la Materia Condensada
Issue Date: 3-Feb-2017
Publisher: Royal Society of Chemistry
Citation: Physical Chemistry Chemical Physics. 2017, 19: 6206-6215. doi:10.1039/C6CP06819G
Abstract: Amphiphilic and lipophilic donor–acceptor naphthalimide–oligothiophene assemblies exhibiting almost identical intramolecular properties, but differing in their intermolecular interactions, have been synthesized. Here we analyze the effect of replacing the normally used lipophilic alkyl chains with hydrophilic ones in directing molecular aggregation from an antiparallel to a parallel stacking. This different molecular packing of the amphiphilic, NIP-3TAmphi, and lipophilic, NIP-3TLipo, systems is assessed by electronic spectroscopies, scanning electronic microscopy and DFT quantum-chemical calculations. Theoretical calculations indicate that the presence of amphiphilic interactions promotes a face-to-face parallel arrangement of neighbor molecules, which induces improved electronic coupling and therefore enhances the charge transport ability and photoconducting properties of this type of materials. Time of flight and photoconducting measurements are used to determine the impact of the amphiphilic and lipophilic interactions on their possible performance in optoelectronic devices.
Sponsor: We thank the MINECO of Spain (MAT2014-52305-P and MAT2016-77608-C3-2-P) and the UCM-BSCH joint project (GR3/14-910759), for financial support at Complutense University of Madrid. Research at University of Malaga was supported by MINECO (CTQ2015-66897-P) and Junta de Andalucia (P09-4708). R. P. O. and I. A.-M. thank the MINECO of Spain for a “Ramón y Cajal” research contract and for a predoctoral fellowship, respectively. The work performed at the University of Alicante was funded by MINECO through grant no. MAT-2011-28167-C02-01.
URI: http://hdl.handle.net/10045/63490
ISSN: 1463-9076 (Print) | 1463-9084 (Online)
DOI: 10.1039/C6CP06819G
Language: eng
Type: info:eu-repo/semantics/article
Rights: © the Owner Societies 2017
Peer Review: si
Publisher version: http://dx.doi.org/10.1039/C6CP06819G
Appears in Collections:INV - Física de la Materia Condensada - Artículos de Revistas

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