Preparation, Supramolecular Organization, and On-Surface Reactivity of Enantiopure Subphthalocyanines: From Bulk to 2D-Polymerization
| Autor: | Sergio Diaz-Tendero Victoria, Jorge Labella Santodomingo, Fernando Aguilar-Galindo, Jorge Lobo-Checa, Leyre Hernández-López, Tomas Torres, Giulia Lavarda |
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| Přispěvatelé: | Ministerio de Ciencia, Innovación y Universidades (España), Agencia Estatal de Investigación (España), Ministerio de Economía y Competitividad (España), European Commission, Ministerio de Educación, Cultura y Deporte (España) |
| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Repositorio Institucional del Instituto Madrileño de Estudios Avanzados en Nanociencia instname |
| ISSN: | 1520-5126 |
| Popis: | The development of chiral materials is severely limited by the challenge to achieve enantiopure derivatives with both configurational stability and good optoelectronic properties. Herein we demonstrate that enantiopure subphthalocyanines (SubPcs) fulfill such demanding requirements and bear the prospect of becoming components of chiral technologies. Particularly, we describe the synthesis of enantiopure SubPcs and assess the impact of chirality on aspects as fundamental as the supramolecular organization, the behavior in contact with metallic surfaces, and the on-surface reactivity and polymerization. We find that enantiopure SubPcs remarkably tend to organize in columnar polar assemblies at the solid state and highly ordered chiral superstructures on Au(111) surfaces. At the metal interface, such SubPcs are singled out by scanning tunneling microscopy. DFT calculations suggest that SubPcs undergo a bowl-to-bowl inversion that was shown to be dependent on the axial substituent. Finally, we polymerize by means of on-surface synthesis a highly regular 2D, porous and chiral, π-extended polymer that paves the way to future nanodevice fabrication. We gratefully acknowledge financial support from the Spanish MINECO and MICINN through Projects PID2020-116490GB-I00, MAT2016-78293-C6-R6, PID2019-107338RBC64, AEI/10.13039/501100011033, RED2018-102833-T, PID2019-110091GB-I00, and the “María de Maeztu” (CEX2018-000805-M) Program for Centers of Excellence in R&D, including the Spanish Research Agency (AEI) and the European Regional Development Fund (ERDF) and the Regional Government of Aragon (E12-20R). IMDEA Nanociencia acknowledges support from the “Severo Ochoa” Programme for Centres of Excellence in R&D (MINECO, Grant SEV2016-0686). J.L. and G.L. acknowledge MECD, Spain, for a F.P.U. fellowship. |
| Databáze: | OpenAIRE |
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