title: Molecular aggregation of naphthalimide organic semiconductors assisted by amphiphilic and lipophilic interactions: a joint theoretical and experimental study.
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.
authors.affiliation: Departamento de Química Física, Universidad de Málaga, Málaga, 29071, Spain. teodomiro@uma.es rocioponce@uma.es.
authors.forename: I
authors.initials: I
authors.lastname: Arrechea-Marcos
authors.affiliation: Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, Madrid, E-28040 Madrid, Spain. segura@quim.ucm.es and Departamento de Tecnología Química y Ambiental, Universidad Rey Juan Carlos, Madrid 28933, Spain.
authors.forename: P
authors.initials: P
authors.lastname: de Echegaray
authors.affiliation: Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, Madrid, E-28040 Madrid, Spain. segura@quim.ucm.es.
authors.forename: M J
authors.initials: MJ
authors.lastname: Mancheño
authors.affiliation: Departamento de Química Física, Universidad de Málaga, Málaga, 29071, Spain. teodomiro@uma.es rocioponce@uma.es.
authors.forename: M C
authors.initials: MC
authors.lastname: Ruiz Delgado
authors.affiliation: Departamento de Tecnología Química y Ambiental, Universidad Rey Juan Carlos, Madrid 28933, Spain.
authors.forename: M M
authors.initials: MM
authors.lastname: Ramos
authors.affiliation: Dpto. Óptica, Instituto Universitario de Materiales de Alicante y Unidad Asociada UA-CSIC, Universidad de Alicante, 03080 Alicante, Spain.
authors.forename: J A
authors.initials: JA
authors.lastname: Quintana
authors.affiliation: Dpto. Física Aplicada, Instituto Universitario de Materiales de Alicante y Unidad Asociada UA-CSIC, Universidad de Alicante, 03080 Alicante, Spain.
authors.forename: J M
authors.initials: JM
authors.lastname: Villalvilla
authors.affiliation: Dpto. Física Aplicada, Instituto Universitario de Materiales de Alicante y Unidad Asociada UA-CSIC, Universidad de Alicante, 03080 Alicante, Spain.
authors.forename: M A
authors.initials: MA
authors.lastname: Díaz-García
authors.affiliation: Departamento de Química Física, Universidad de Málaga, Málaga, 29071, Spain. teodomiro@uma.es rocioponce@uma.es.
authors.forename: J T
authors.initials: JT
authors.lastname: López Navarrete
authors.affiliation: Departamento de Química Física, Universidad de Málaga, Málaga, 29071, Spain. teodomiro@uma.es rocioponce@uma.es.
authors.forename: R
authors.identifier: http://orcid.org/0000-0002-3836-3494
authors.initials: R
authors.lastname: Ponce Ortiz
authors.affiliation: Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, Madrid, E-28040 Madrid, Spain. segura@quim.ucm.es.
authors.forename: J L
authors.initials: JL
authors.lastname: Segura