Helical nanostructures for organic electronics: the role of topological sulfur in ad hoc synthesized dithia[7]helicenes studied in the solid state and on a gold surface
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Título: | Helical nanostructures for organic electronics: the role of topological sulfur in ad hoc synthesized dithia[7]helicenes studied in the solid state and on a gold surface |
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Autor/es: | Baciu, Bianca C. | Ara, Tamara de | Sabater, Carlos | Untiedt, Carlos | Guijarro, Albert |
Grupo/s de investigación o GITE: | Nuevos Materiales y Catalizadores (MATCAT) | Grupo de Nanofísica |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Física Aplicada | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Materiales | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Helical nanostructures | Organic electronics | Topological sulfur | Dithia[7]helicenes | Solid state | Gold surface |
Área/s de conocimiento: | Física Aplicada | Física de la Materia Condensada | Química Orgánica |
Fecha de publicación: | 16-mar-2020 |
Editor: | Royal Society of Chemistry |
Cita bibliográfica: | Nanoscale Advances. 2020, 2: 1921-1926. doi:10.1039/D0NA00045K |
Resumen: | As the first of a series of molecular solenoids, two classes of dithia[7]helicenes (coil-shaped molecules with sulfur atoms integrated within a helical conjugated system) have been devised and synthesized to be used in molecular electronics. We used a modular assembly of fragments using Pd catalyzed coupling reactions and a final photocyclization step for the syntheses; this strategy gave us straightforward access to helicenes bearing thiophene end rings with either exo or endo topologies. Unequivocal structural characterization was carried out by X-ray crystallography. In the solid state, their crystal architectures show little similarities; both can be considered an ensemble of heterochiral dimers (P/M) that are themselves very different in nature in light of their main pairing interactions. On a gold surface, the effect of the sulfur atom is to strengthen their binding to the electrodes, as manifested by scanning tunneling microscopy (STM) performed at room temperature. Different coating patterns were observed for each class of molecule, although the most prominent finding is that we could see resolved STM images of a single molecule, with a full display of its inherent chirality under room temperature conditions. |
Patrocinador/es: | Financial support by the Spanish Ministry of Economy and Competitiveness (MAT2016-78625-C2-1-P and MAT2016-78625-C2-2-P), the Generalitat Valenciana (PROMETEO/2017/139 and CDEIGENT/2018/028), and finally the University of Alicante (VIGROB-285 and 188) is gratefully acknowledged. |
URI: | http://hdl.handle.net/10045/107376 |
ISSN: | 2516-0230 |
DOI: | 10.1039/D0NA00045K |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | This article is licensed under a Creative Commons Attribution 3.0 Unported Licence |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.1039/D0NA00045K |
Aparece en las colecciones: | INV - MATCAT - Artículos de Revistas INV - Grupo de Nanofísica - Artículos de Revistas |
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