ABSTRACT
Acene-based molecular materials have been demonstrated to be useful semiconductors and chromophores. For example, pentacene and rubrene are among the top most studied molecules used in active layer in organic field effect transistors (OFETs) with high hole mobilities. Longer acenes can be also used as model compounds to investigate zig-zag edges of graphene. However, one drawback which hampers their general applications is their intrinsic instability. Typical reactions of acenes related to the diene conjugation include addition with singlet oxygen to form endoperoxide and dimerization under light irradiation. In addition, parent acenes usually have poor solubility in common organic solvents. Therefore, we have developed several strategies to stabilize and solubilize acene based molecules, and a few kinds of acene derivatives have been prepared. They include n-type acenes, higher order acenes and quinoidal heteroacenes. Their physical properties and applications have been studied.
REFERENCES
[1] A. N. Lakshminarayana, J. Chang, J. Luo, B. Zheng, K.-W. Huang, C. Chi*, Chem. Commun. 2015, 51, DOI: 10.1039/c4cc09812a. [2] Q. Ye, C. Chi*, “Recent Highlights and Perspectives on Acene Based Molecules and Materials”, Chem. Mater., 2014, 26, 4046. [3] X. Shi, P. M. Burrezo, S. Lee, W. Zhang, B. Zheng, G. Dai, J. Chang, J.
T. L. Navarrete, K.-W. Huang, D. Kim, J. Casado, C. Chi*, “Antiaromatic Bisindeno-[n]thienoacenes With Small Singlet Biradical Characters: Syntheses, Structures and Chain Length Dependent Physical Properties” Chem. Sci. 2014, 5, 4490. [4] X. Shi, J. Chang, C. Chi*, “Solution-processable n-type and ambipolar semiconductors based on a fused cyclopentadithiophenebis(dicyanovinylene) core” Chem. Commun. 2013, 49, 7135. [5] Z. Sun, Q. Ye, C. Chi*, J. Wu*, “Low band gap polycyclic hydrocarbons: from closed-shell near infrared dyes and semiconductors to open-shell radicals” Chem. Soc. Rev., 2012, 41,7857. [6] H. Qu, W. Cui, J. Li, J. Shao, C. Chi*, “6, 13-Dibromopentacene [2,3:9,10]-Bis(dicarboximide): A Versatile Building Block for Stable Pentacene Derivatives” Org. Lett., 2011, 13, 924.