Abstract
Compact molecular packing with short π-π stacking and large π-overlap in organic semiconductors is desirable for efficient charge transport and high carrier mobility. Thus charge transport anisotropy along different directions is commonly observed in organic semiconductors. Interestingly, in this article, we found that comparable charge transport property were achieved based on the single crystals of a bis-fused tetrathiafulvalene derivative (EM-TTP) compound along two interaction directions, that is, the multiple strong S···S intermolecular interactions and the π-π stacking direction, with the measured electrical conductivity and hole mobility of 0.4 S cm−1, 0.94 cm2 V−1 s−1 and 0.2 S cm−1, 0.65 cm2 V−1 s−1, respectively. This finding provides us a new molecular design concept for developing novel organic semiconductors with isotropic charge transport property through the synergistic effect of multiple intermolecular interactions (such as S···S interactions) and π-π stacking.
Similar content being viewed by others
References
Someya T, Bao Z, Malliaras GG. Nature, 2016, 540: 379–385
Dong H, Fu X, Liu J, Wang Z, Hu W. Adv Mater, 2013, 25: 6158–6183
Melzer C, von Seggern H. Nat Mater, 2010, 9: 470?472
Wang C, Dong H, Hu W, Liu Y, Zhu D. Chem Rev, 2012, 112: 2208–2267
Wang C, Zhang J, Long G, Aratani N, Yamada H, Zhao Y, Zhang Q. Angew Chem Int Ed, 2015, 54: 6292–6296
Kabe R, Notsuka N, Yoshida K, Adachi C. Adv Mater, 2016, 28: 655–660
Zhou Y, Cheun H, Choi S, Potscavage Jr WJ, Fuentes-Hernandez C, Kippelen B. Appl Phys Lett, 2010, 97: 153304
Zhou K, Dong H, Zhang H, Hu W. Phys Chem Chem Phys, 2014, 16: 22448–22457
Fan H, Zhu X. Sci China Chem, 2015, 58: 922–936
Yu T, Liu L, Xie Z, Ma Y. Sci China Chem, 2015, 58: 907–915
Giri G, Verploegen E, Mannsfeld SCB, Atahan-Evrenk S, Kim DH, Lee SY, Becerril HA, Aspuru-Guzik A, Toney MF, Bao Z. Nature, 2011, 480: 504–508
Diao Y, Tee BCK, Giri G, Xu J, Kim DH, Becerril HA, Stoltenberg RM, Lee TH, Xue G, Mannsfeld SCB, Bao Z. Nat Mater, 2013, 12: 665–671
Janneck R, Vercesi F, Heremans P, Genoe J, Rolin C. Adv Mater, 2016, 28: 8007–8013
Li G, Zhao Y, Li J, Cao J, Zhu J, Sun XW, Zhang Q. J Org Chem, 2015, 80: 196–203
Chen W, Yang X, Long G, Wan X, Chen Y, Zhang Q. J Mater Chem C, 2015, 3: 4698–4705
Zhang X, Chen X, Liu J, Zhen Y, Dong H, Li L, Hu W. Sci China Chem, 2016, 59: 1645–1650
Shirota Y, Kageyama H. Chem Rev, 2007, 107: 953–1010
Dong H, Wang C, Hu W. Chem Commun, 2010, 46: 5211–5222
Leufgen M, Rost O, Gould C, Schmidt G, Geurts J, Molenkamp LW, Oxtoby NS, Mas-Torrent M, Crivillers N, Veciana J, Rovira C. Org Electron, 2008, 9: 1101–1106
Mas-Torrent M, Durkut M, Hadley P, Ribas X, Rovira C. J Am Chem Soc, 2004, 126: 984–985
Mas-Torrent M, Hadley P, Bromley ST, Ribas X, Tarrés J, Mas M, Molins E, Veciana J, Rovira C. J Am Chem Soc, 2004, 126: 8546–8553
Takahashi Y, Hasegawa T, Horiuchi S, Kumai R, Tokura Y, Saito G. Chem Mater, 2007, 19: 6382–6384
Misaki Y. Sci Technol Adv Mater, 2016, 10: 024301
Fang Q, Chen H, Lei H, Xue G, Chen X. CrystEngComm, 2015, 17: 787–796
Jiang L, Gao J, Wang E, Li H, Wang Z, Hu W, Jiang L. Adv Mater, 2008, 20: 2735–2740
Li R, Hu W, Liu Y, Zhu D. Acc Chem Res, 2010, 43: 529–540
Tang Q, Jiang L, Tong Y, Li H, Liu Y, Wang Z, Hu W, Liu Y, Zhu D. Adv Mater, 2008, 20: 2947–2951
Kobayashi Y, Terauchi T, Sumi S, Matsushita Y. Nat Mater, 2016, 16: 109–114
Kobayashi A, Fujiwara E, Kobayashi H. Chem Rev, 2004, 104: 5243–5264
Saito G, Yoshida Y. Bull Chem Soc Jpn, 2007, 80: 1–137
Schwierz F. Nat Nanotech, 2010, 5: 487–496
Acknowledgments
This work was supported by the Ministry of Science and Technology of China (2016YFB0401100, 2013CB933403, 2013CB933504), the National Natural Science Foundation of China (51633006, 91433115, 51222306, 91222203, 91233205, 21472116), Chinese Academy of Sciences (XDB12030300), Beijing NOVA Programmer (Z131101000413038), Beijing Local College Innovation Team Improve Plan (IDHT20140512), and Youth Innovation Promotion Association CAS.
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
11426_2016_9011_MOESM1_ESM.pdf
Comparable charge transport property based on S···S interactions with that of π-π stacking in a bis-fused tetrathiafulvalene compound
Rights and permissions
About this article
Cite this article
Zhou, K., Chen, H., Dong, H. et al. Comparable charge transport property based on S···S interactions with that of π-π stacking in a bis-fused tetrathiafulvalene compound. Sci. China Chem. 60, 510–515 (2017). https://doi.org/10.1007/s11426-016-9011-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-016-9011-9