Bis(arylene-ethynylene)-s-tetrazines: A Promising Family of n-Type Organic Semiconductors?

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• 作者：M贸nica Moral ; Andr茅s Garz贸n ; Yoann Olivier ; Luca Muccioli ; Juan Carlos Sancho-Garc铆a ; Jos茅 M. Granadino-Rold谩n ; Manuel Fern谩ndez-G贸mez
• 刊名：Journal of Physical Chemistry C
• 出版年：2015
• 出版时间：August 20, 2015
• 年：2015
• 卷：119
• 期：33
• 页码：18945-18955
• 全文大小：850K
• ISSN：1932-7455

文摘

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鈥?.3 cm² V^鈥? s^鈥?, 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.