(Invited) Distorted Aromatics and Their Related 1D and 2D Materials

Abstract

Polycyclic aromatic hydrocarbons (PAHs) are receiving a great deal of attention because of their increasingly better performance in organic electronic applications. Among these, PAHs containing N atoms (N-PAHs) are particularly interesting since their electronic structure, stability, solubility, and supramolecular organization can be modulated by varying the number and position of N atoms. In general, PAHs are planar structures but they can adopt twisted conformations as the result of the steric strain induced by overcrowding or congestion in key positions of the aromatic core. twisted-PAHs have shown enhanced solubility and unique optoelectronic and chiroptical properties as an effect of their distorted molecular structure. We have developed a general strategy that provides access to a new family of twisted-N-PAHs (0D) with different twist angles by introducing silyl groups with different size and rigidity, providing direct experimental correlation between twist size and properties. In addition, this methodology has been successfully implemented in the preparation of 1D and 2D materials. The most recent advances of these materials including synthetic routes, optoelectronic properties, self-organising properties, and potential applications will be discussed. References [11] L. Jiang, A.C. Papageorgiou,* S. Cheol; Ö. Sağlam, J. Reichert,* D.A. Duncan, Y.-Q. Zhang, F. Klappenberger; S. More, R. Bhosale, A. Mateo-Alonso* and J.V. Barth ACS Nano 2016,DOI: 10.1021/acsnano.5b06340. [10] A. Mateo-Alonso Chem. Soc. Rev. 2014, 43, 6311-6324. [9] A.B. Marco, D. Cortizo-Lacalle, C. Gozalvez, M. Olano, A. Atxabal, X. Sun, M. Melle-Franco, L.E. Hueso, and A. Mateo-Alonso Chem. Comm. 2015, 51, 10754-10757. [8] R. Garcia, M. Melle-Franco and A. Mateo-Alonso Chem. Comm. 2015, 51, 8037-8040.[7] R. García, S. More, M. Melle-Franco, A. Mateo-Alonso Org. Lett. 2014, 16, 6096−6099. [6] G. Tregnago, C. Fléchon, S. Choudhary, C. Gozalvez, A. Mateo-Alonso, F. Cacialli App. Phys. Lett., 2014, 105, 143304. [5] S. More, R. Bhosale, A. Mateo-Alonso Chem. Eur. J., 2014, 20, 10626-10631. [4] S. More, S. Choudhary, A. Higelin, I. Krossing, M. Melle-Franco, A. Mateo-Alonso Chem. Comm., 2014, 50, 1976-1979. [3] S. Choudhary, C. Gozalvez, A. Higelin, I. Krossing, M. Melle-Franco, A. Mateo-Alonso Chem. Eur. J., 2014, 20, 1525-1528. [2] S. More, R. Bhosale, S. Choudhary, A. Mateo-Alonso Org. Lett. 2012, 14, 4170-4173. [1] N. Kulisic, S. More, and A. Mateo-Alonso Chem. Comm. 2011, 47, 514-516.