TY - JOUR
T1 - Bis(arylene-ethynylene)-s-tetrazines
T2 - A Promising Family of n-Type Organic Semiconductors?
AU - Moral, Mónica
AU - Garzón, Andrés
AU - Olivier, Yoann
AU - Muccioli, Luca
AU - Sancho-García, Juan Carlos
AU - Granadino-Roldán, José M.
AU - Fernández-Gómez, Manuel
PY - 2015/8/20
Y1 - 2015/8/20
N2 - We theoretically describe in this work the n-type semiconducting behavior of a set of bis(arylene-ethynylene)-s-tetrazines ((ArCC)2Tz), by comparing their electronic properties with those of their parent diaryl-s-tetrazines (Ar2Tz) after the introduction of ethynylene bridges. The significantly reduced internal reorganization energy for electron transfer is ascribed to an extended delocalization of the LUMO for (ArCC)2Tz as opposite to that for Ar2Tz, which was described mostly localized on the s-tetrazine ring. The largest electronic coupling and the corresponding electron transfer rates found for bis(phenyl-ethynylene)-s-tetrazine, as well as for some halogenated derivatives, are comparable to those reported for the best performing n-type organic semiconductor materials such as diimides and perylenes. The theoretical mobilities for the studied compounds turn out to be in the range 0.3-1.3 cm2 V-1 s-1, close to values experimentally determined for common n-type organic semiconductors used in real devices. In addition, ohmic contacts can be expected when these compounds are coupled to metallic cathodes such as Na, Ca, and Sm. For these reasons, the future application of semiconducting bis(phenyl-ethynylene)-s-tetrazine and its fluorinated and brominated derivatives in optoelectronic devices is envisioned.
AB - We theoretically describe in this work the n-type semiconducting behavior of a set of bis(arylene-ethynylene)-s-tetrazines ((ArCC)2Tz), by comparing their electronic properties with those of their parent diaryl-s-tetrazines (Ar2Tz) after the introduction of ethynylene bridges. The significantly reduced internal reorganization energy for electron transfer is ascribed to an extended delocalization of the LUMO for (ArCC)2Tz as opposite to that for Ar2Tz, which was described mostly localized on the s-tetrazine ring. The largest electronic coupling and the corresponding electron transfer rates found for bis(phenyl-ethynylene)-s-tetrazine, as well as for some halogenated derivatives, are comparable to those reported for the best performing n-type organic semiconductor materials such as diimides and perylenes. The theoretical mobilities for the studied compounds turn out to be in the range 0.3-1.3 cm2 V-1 s-1, close to values experimentally determined for common n-type organic semiconductors used in real devices. In addition, ohmic contacts can be expected when these compounds are coupled to metallic cathodes such as Na, Ca, and Sm. For these reasons, the future application of semiconducting bis(phenyl-ethynylene)-s-tetrazine and its fluorinated and brominated derivatives in optoelectronic devices is envisioned.
UR - http://www.scopus.com/inward/record.url?scp=84939832548&partnerID=8YFLogxK
U2 - 10.1021/acs.jpcc.5b05015
DO - 10.1021/acs.jpcc.5b05015
M3 - Article
AN - SCOPUS:84939832548
SN - 1932-7447
VL - 119
SP - 18945
EP - 18955
JO - Journal of Physical Chemistry C: Nanomaterials and interfaces
JF - Journal of Physical Chemistry C: Nanomaterials and interfaces
IS - 33
ER -