Academic Journal
Dual-mode chiral self-assembly of cone-shaped subphthalocyanine aromatics
| العنوان: | Dual-mode chiral self-assembly of cone-shaped subphthalocyanine aromatics |
|---|---|
| المؤلفون: | Mayoral, María J., Guilleme, Julia, Calbo, Joaquín, Aragó, Juan, Aparicio, Fátima, Ortí, Enrique, Torres, Tomás, González-Rodríguez, David |
| المساهمون: | UAM. Departamento de Química Orgánica |
| بيانات النشر: | American Chemical Society |
| سنة النشر: | 2021 |
| المجموعة: | Universidad Autónoma de Madrid (UAM): Biblos-e Archivo |
| مصطلحات موضوعية: | Self-assembly, Subphthalocyanine, Supramolecular Polymers, Porphyrinoids, Química |
| الوصف: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.0c07291 ; Columnar polymers and liquid crystals obtained from π-conjugated cone-shaped molecules are receiving increasing interest due to the possibility of obtaining unconventional polar organizations that show anisotropic charge transport and unique chiroptical properties. However, and in contrast to the more common planar discotics, the self-assembly of conic or pyramidic molecules in solution remains largely unexplored. Here, we show how a molecular geometry change, from flat to conic, can generate supramolecular landscapes where different self-assembled species, each of them being under thermodynamic equilibrium with the monomer, exist exclusively within distinct regimes. In particular, depending on the solvent nature-aromatic or aliphatic-cone-shaped C3-symmetric subphthalocyanine 1 can undergo self-assembly either as a tail-to-tail dimer, showing monomer-dimer sigmoidal transitions, or as a head-to-tail noncentrosymmetric columnar polymer, exhibiting a nucleation-elongation polymerization mechanism. Moreover, the experimental and theoretical comparison between racemic and enantiopure samples revealed that the two enantiomers (1M and 1P) tend to narcissistically self-sort in the dimer regime, each enantiomer showing a strong preference to associate with itself, but socially self-sort in the polymer regime, favoring an alternate stacking order along the columns ; Funding from the Spanish MINECO/MCIU [PGC2018-099568-B-I00, CTQ2017-85393-P, CTQ2017-84727-P, ERA-NET/European Commission/MINECO (UNIQUE, SOLAR-ERA.NET Cofund 2 N° 008/ PCI2019-111889-2), and RED2018-102331-T], the Generalitat Valenciana (SEJI/2018/035), and European Feder funds (PGC2018-099568-B-I00) is gratefully acknowledged. IMDEA ... |
| نوع الوثيقة: | article in journal/newspaper |
| وصف الملف: | application/pdf |
| اللغة: | English |
| Relation: | Journal of the American Chemical Society; https://doi.org/10.1021/jacs.0c07291; Gobierno de España. PGC2018-099568-B-I00; Gobierno de España. CTQ2017-85393-P; Gobierno de España. CTQ2017-84727-P; Gobierno de España. PCI2019-111889-2; Gobierno de España. RED2018-102331-T; Gobierno de España. SEV-2016-0686; Journal of the American Chemical Society (JACS) 142.50 (2020): 21017-21031; 0002-7863 (print); 1520-5126 (online); http://hdl.handle.net/10486/698339; 21017; 50; 21031; 142 |
| DOI: | 10.1021/jacs.0c07291 |
| الاتاحة: | http://hdl.handle.net/10486/698339 https://doi.org/10.1021/jacs.0c07291 |
| Rights: | © 2020 American Chemical Society ; openAccess |
| رقم الانضمام: | edsbas.4F33234C |
| قاعدة البيانات: | BASE |
| DOI: | 10.1021/jacs.0c07291 |
|---|