TY - JOUR
T1 - Benzotrithiophene versus Benzo/Naphthodithiophene Building Blocks
T2 - The Effect of Star-Shaped versus Linear Conjugation on Their Electronic Structures
AU - Riaño, Alberto
AU - Arrechea-Marcos, Iratxe
AU - Mancheño, María J.
AU - Mayorga Burrezo, Paula
AU - De La Peña, Alejandro
AU - Loser, Stephen
AU - Timalsina, Amod
AU - Facchetti, Antonio
AU - Marks, Tobin J.
AU - Casado, Juan
AU - López Navarrete, J. Teodomiro
AU - Ponce Ortiz, Rocío
AU - Segura, José L.
N1 - Funding Information:
We thank the MINECO of Spain (MAT2014-52305-P) and the UCM-BSCH joint project (GR3/14-910759) for financial support at Complutense University of Madrid. We also thank AFOSR (FA9550-08-01-0331) and the NSF-MRSEC program through the Northwestern Materials Research Center (DMR-1121262) for support of this research at Northwestern University. Research at University of Malaga was supported by MINECO (CTQ2012-33733) and Junta de Andalucia (P09-4708). R.P.O. thanks MINECO for a "Ram?n y Cajal" research contract. A.R. and I.A.M. acknowledge the MINECO of Spain for predoctoral fellowships.
PY - 2016/4/25
Y1 - 2016/4/25
N2 - The synthesis, characterization, and optical properties of a novel star-shaped oligothiophene with a central rigid trithienobenzene (BTT) core and diketopyrrolopyrrole (DPP) units are reported and compared with homologous linear systems based on the benzodithiophene (BDT) and the naphthodithiophene (NDT) units end capped with DPPs. This comparison is aimed at elucidating the effect of the star-shaped configuration versus linear conformation on the optical and electrical properties. Electronic and vibrational spectroscopies, together with transient absorption spectroscopy, scanning electronic microscopy, and DFT calculations are used to understand not only the molecular properties of these semiconductors, but also to analyze the supramolecular aggregation in these derivatives. We conclude that although the subject star-shaped derivative is not optimal in terms of π-conjugation, its extended BTT unit significantly favors intermolecular π-stacking interactions, which is interesting for their applications in devices. Field-effect transistors and solar cells were fabricated with these new molecular semiconductors and the performance difference discussed.
AB - The synthesis, characterization, and optical properties of a novel star-shaped oligothiophene with a central rigid trithienobenzene (BTT) core and diketopyrrolopyrrole (DPP) units are reported and compared with homologous linear systems based on the benzodithiophene (BDT) and the naphthodithiophene (NDT) units end capped with DPPs. This comparison is aimed at elucidating the effect of the star-shaped configuration versus linear conformation on the optical and electrical properties. Electronic and vibrational spectroscopies, together with transient absorption spectroscopy, scanning electronic microscopy, and DFT calculations are used to understand not only the molecular properties of these semiconductors, but also to analyze the supramolecular aggregation in these derivatives. We conclude that although the subject star-shaped derivative is not optimal in terms of π-conjugation, its extended BTT unit significantly favors intermolecular π-stacking interactions, which is interesting for their applications in devices. Field-effect transistors and solar cells were fabricated with these new molecular semiconductors and the performance difference discussed.
KW - field-effect transistors
KW - oligothiophene
KW - optical properties
KW - semiconductors
KW - solar cells
KW - π-stacking interactions
UR - http://www.scopus.com/inward/record.url?scp=84961836747&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84961836747&partnerID=8YFLogxK
U2 - 10.1002/chem.201504526
DO - 10.1002/chem.201504526
M3 - Article
C2 - 26999589
AN - SCOPUS:84961836747
VL - 22
SP - 6374
EP - 6381
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 18
ER -