TY - JOUR
T1 - Engineering organic semiconducting solids. Multicomponent access to crystalline 3-(4-aryl-1,2,3-triazolyl)coumarins
AU - De La Cerda-Pedro, J. E.
AU - Arcos-Ramos, R.
AU - Maldonado-Domínguez, M.
AU - Rojas-Lima, S.
AU - Romero-Ávila, M.
AU - Carreón-Castro, M. P.
AU - Santillan, R.
AU - Farfán, N.
AU - López-Ruiz, H.
N1 - Publisher Copyright:
© The Royal Society of Chemistry 2016.
PY - 2016
Y1 - 2016
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84979517515&partnerID=8YFLogxK
U2 - 10.1039/c6ce01041e
DO - 10.1039/c6ce01041e
M3 - Artículo
SN - 1466-8033
VL - 18
SP - 5562
EP - 5571
JO - CrystEngComm
JF - CrystEngComm
IS - 29
ER -