Halogenated Thienoacene Derivatives with Improved Emission Properties

Abstract

Thienoacenes is one of most important groups of semiconducting materials due to the high stability and superior mobility. However, there are scarce studies on the emission properties of thienoacenes to date. Herein, we synthesized fluorinated and chlorinated dibenzo[d,d’]thieno[3,2-b;4,5-b’]dithiophenes (DBTDTs) derivatives F6-DBTDT and Cl6-DBTDT by sulfoxide cyclization, significantly lowering the energy levels relative to the parent compound DBTDT. According to single crystal structure analysis, F6-DBTDT molecules adopt one-dimensional slipped stacking with close π-π interactions of 3.43 Å (1 Å=0.1 nm), which is different from the parent compound DBTDT with herringbone stacking motif. Interestingly, the halogenated DBTDT derivatives exhibit enhanced emission properties both in solution and in the solid state, opening up possiblities to improve photoluminescence of thienoacences by halogenation.

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Keywords

Thienoacene / Halogenation / Photoluminescence / Aggregation structure

References

[1] Takimiya K, Shinamura S, Osaka I, Miyazaki E. Adv. Mater., 2011, 23: 4347.

[2] Takimiya K, Ebata H, Sakamoto K, Izawa T, Otsubo T, Kunugi Y. J. Am. Chem. Soc., 200, 128: 12604.

[3] He P, Tu Z, Zhao G, Zhen Y, Geng H, Yi Y, Wang Z, Zhang H, Xu C, Liu J, Lu X, Fu X, Zhao Q, Zhang X, Ji D, Jiang L, Dong H, Hu W. Adv. Mater., 2015, 27: 825.

[4] Zhang H, Yu X, Li M, Zhang Z, Song Z, Zong X, Duan G, Zhang W, Chen C, Zhang W-H, Liu Y, Liang M. Angew. Chem. Int. Ed., 2023, 62: e202314270.

[5] Huang J, Wang W, Zhang L, Meng X. Chin. Chem. Lett., 2023, 34: 108003.

[6] Ebata H, Izawa T, Miyazaki E, Takimiya K, Ikeda M, Kuwabara H, Yui T. J. Am. Chem. Soc., 2007, 129: 15732.

[7] Gao J H, Li R J, Li L Q, Meng Q, Jiang H, Li H X, Hu W P. Adv. Mater., 2007, 19: 3008.

[8] Li R, Jiang L, Meng Q, Gao J, Li H, Tang Q, He M, Hu W, Liu Y, Zhu D. Adv. Mater., 2009, 21: 4492.

[9] Miyata Y, Yoshikawa E, Minari T, Tsukagoshi K, Yamaguchi S. J. Mater. Chem., 2012, 22: 7715.

[10] Liu S, Fang X, Lu B, Yan D. Nat. Commun., 2020, 11: 4649.

[11] Huang Y, Xing J, Gong Q, Chen L-C, Liu G, Yao C, Wang Z, Zhang H-L, Chen Z, Zhang Q. Nat. Commun., 2019, 10: 169.

[12] An Z, Zheng C, Tao Y, Chen R, Shi H, Chen T, Wang Z, Li H, Deng R, Liu X, Huang W. Nat. Mater., 2015, 14: 685.

[13] Liu J, Zhang H, Dong H, Meng L, Jiang L, Jiang L, Wang Y, Yu J, Sun Y, Hu W, Heeger A J. Nat. Commun., 2015, 6: 10032.

[14] Guo R, Zhang J, Jia X, Shi C, Qie F, Zhen Y. Chem. Res. Chinese Universities, 2023, 39: 1106.

[15] Qin Z, Wang T, Gao H, Li Y, Dong H, Hu W. Adv. Mater., 2023, 35: 2301955.

[16] Eshun A, Cai Z, Awies M, Yu L, Goodson T. J. Phys. Chem. A, 2018, 122: 8167.

[17] Zhu L, Liu Y, Wang X, Zhang K, Tai J-W, Sun Y-Q, Wang C-K, Ding L, Fung M-K, Fan J. Chem. Eng. J., 2023, 473: 145449.

[18] Sirringhaus H, H. Friend R, Wang C, Leuninger J, Müllen K. J. Mater. Chem., 1999, 9: 2095.

[19] Xiong Y, Qiao X, Wu H, Huang Q, Wu Q, Li J, Gao X, Li H. J. Org. Chem., 2014, 79: 1138.

[20] Miyata Y., Suzuki Y., Preparation of Bis(benzo[4,5]chalcogeno) [3,2-c:2′3′-e]chalcogenophenes under Mild Conditions, WO2012137694, 2012.

[21] Okamoto T, Kudoh K, Wakamiya A, Yamaguchi S. Org. Lett., 2005, 7: 5301.

[22] Yu P, Zhen Y, Dong H, Hu W. Chem., 2019, 5: 2814.

[23] Wang Y, Hu Y, Guo J, Wang Z, Li Y, Qie F, Shi C, Zhang L, Zhen Y. Sci. China Chem., 2023, 66: 1450.

[24] Wang Z, Hu Y, Xie Y, Qie F, Guo J, Zhang L, Shi C, Glöcklhofer F, Zhen Y. Sci. China Mater., 2023, 66: 2429.

[25] Hestand N J, Spano F C. Chem. Rev., 2018, 118: 7069.

[26] Spano F C. Acc. Chem. Res., 2010, 43: 429.

[27] Liu J, Zhu W, Zhou K, Wang Z, Zou Y, Meng Q, Li J, Zhen Y, Hu W. J. Mater. Chem. C, 201, 4: 3621.