Engineering organic semiconducting solids. Multicomponent access to crystalline 3-(4-aryl-1,2,3-triazolyl)coumarinsElectronic supplementary information (ESI) available: Synthetic procedures, 1H and 13C solution NMR and related crystallographic data. CCDC 1455633 (5a), 1455634 (5b), 1455635 (5c), 1455636 (5f), 1455637 (5h), 1455638 (5j), 1455639 (5k) and 1455640 (5l). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6ce01041e

• Main Authors: de la Cerda-Pedro, J. E, Arcos-Ramos, R, Maldonado-Domínguez, M, Rojas-Lima, S, Romero-Ávila, M, Carreón-Castro, M. P, Santillan, R, Farfán, N, López-Ruiz, H
• Format: Journal Article
• Published: 19.07.2016
• ISSN: 1466-8033
• DOI: 10.1039/c6ce01041e

Crystalline 3-(4-aryl-1,2,3-triazol-1-yl)coumarins (ATCs) were prepared from commercial materials using a four-component methodology as a key step. In the present work, a feasible and environmentally friendly route to the title compounds was developed through the reaction between salicylaldehydes, ethyl bromoacetate, phenylacetylenes and sodium azide under mild conditions, with short reaction times and a simple workup. Crystalline solids are readily accessed from the featured products via solution processing and their arrays in the solid state were elucidated through SXRD; these molecules display a periodic overlap of π-systems, which facilitates carrier transport in organic electronic devices. Semiconductor band gaps for the obtained solids were derived through plane-wave DFT and compared with reference systems known to display superior performance in organic electronics. Thus ATCs represent attractive systems for research and implementation in molecular materials, a task which will be facilitated by the concise route herein described. Crystalline arrays of ATCs [3-(4-aryl-1,2,3-triazol-1-yl)coumarins] with periodic stacking and semiconducting character can be successfully engineered.