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Issue 29, 2016
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Engineering organic semiconducting solids. Multicomponent access to crystalline 3-(4-aryl-1,2,3-triazolyl)coumarins

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Abstract

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.

Graphical abstract: Engineering organic semiconducting solids. Multicomponent access to crystalline 3-(4-aryl-1,2,3-triazolyl)coumarins

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Supplementary files

Article information


Submitted
03 May 2016
Accepted
03 Jun 2016
First published
03 Jun 2016

CrystEngComm, 2016,18, 5562-5571
Article type
Paper

Engineering organic semiconducting solids. Multicomponent access to crystalline 3-(4-aryl-1,2,3-triazolyl)coumarins

J. E. de la Cerda-Pedro, R. Arcos-Ramos, M. Maldonado-Domínguez, S. Rojas-Lima, M. Romero-Ávila, M. P. Carreón-Castro, R. Santillan, N. Farfán and H. López-Ruiz, CrystEngComm, 2016, 18, 5562
DOI: 10.1039/C6CE01041E

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