Three-Bladed Rylene Propellers with Three-Dimensional Network Assembly for Organic Electronics

Journal of the American Chemical Society

Volumn 138, Issue 32, 2016, Pages 10184-10190

  Meng, Dong ^a,f   Fu, Huiting ^a,b,f   Xiao, Chengyi ^a,f   Meng, Xiangyi ^d   Winands, Thorsten ^c   Ma, Wei ^d   Wei, Wei ^e   Fan, Bingbing ^b   Huo, Lijun ^b   Doltsinis, Nikos L ^c   Li, Yan ^a   Sun, Yanming ^b   Wang, Zhaohui ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b BEIHANG UNIVERSITY   (China)

^c UNIVERSITY OF MÜNSTER   (Germany)

^d XI'AN JIAOTONG UNIVERSITY   (China)

^e CAPITAL NORMAL UNIVERSITY   (China)

^f UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON TRANSPORT PROPERTIES; MOLECULES; POLYMER SOLAR CELLS; PROPELLERS; SINGLE CRYSTALS; X RAY DIFFRACTION;

HIGH ELECTRON MOBILITY; HIGH POWER CONVERSION; INTERMOLECULAR INTERACTIONS; NEIGHBORING MOLECULES; ORGANIC ELECTRONICS; SINGLE-CRYSTAL TRANSISTORS; SINGLE-CRYSTAL X-RAY DIFFRACTION STUDIES; THREE-DIMENSIONAL NETWORKS;

SINGLE ELECTRON TRANSISTORS;

CHLOROFORM; NITROGEN; PERYLENE; SELENIUM;

ABSORPTION; ABSORPTION SPECTROSCOPY; ARTICLE; ATOMIC FORCE MICROSCOPY; BROMINATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONFORMATION; CRYSTAL; CURRENT DENSITY; CYCLIC POTENTIOMETRY; DENSITY FUNCTIONAL THEORY; ELECTRIC POTENTIAL; ELECTRON; ELECTRON TRANSPORT; ELECTRONICS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR INTERACTION; PHASE SEPARATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; RADIATION SCATTERING; REDUCTION; SHORT CIRCUIT CURRENT; STEREOISOMERISM; SURFACE PROPERTY; SUZUKI REACTION; SYNTHESIS; THERMOGRAVIMETRY; X RAY DIFFRACTION;

EID: 84983656999     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b04368     Document Type: Article

References (38)

1. Jiang, W.; Li, Y.; Wang, Z. Acc. Chem. Res. 2014, 47, 3135-3147 10.1021/ar500240e
2. Ball, M.; Zhong, Y.; Wu, Y.; Schenck, C.; Ng, F.; Steigerwald, M.; Xiao, S.; Nuckolls, C. Acc. Chem. Res. 2015, 48, 267-276 10.1021/ar500355d
3. Pschirer, N. G.; Kohl, C.; Nolde, F.; Qu, J.; Müllen, K. Angew. Chem., Int. Ed. 2006, 45, 1401-1404 10.1002/anie.200502998
4. Yuan, Z.; Lee, S.-L.; Chen, L.; Li, C.; Mali, K. S.; De Feyter, S.; Müllen, K. Chem.-Eur. J. 2013, 19, 11842-11846 10.1002/chem.201302086
5. Weil, T.; Vosch, T.; Hofkens, J.; Peneva, K.; Müllen, K. Angew. Chem., Int. Ed. 2010, 49, 9068-9093 10.1002/anie.200902532
6. Langhals, H.; Schönmann, G.; Feiler, L. Tetrahedron Lett. 1995, 36, 6423-6424 10.1016/0040-4039(95)01276-N
7. Langhals, H.; Zgela, D.; Lüling, R. J. Org. Chem. 2015, 80, 12146-12150 10.1021/acs.joc.5b02092
8. Qian, H.; Wang, Z.; Yue, W.; Zhu, D. J. Am. Chem. Soc. 2007, 129, 10664-10665 10.1021/ja0740972
9. Qian, H.; Negri, F.; Wang, C.; Wang, Z. J. Am. Chem. Soc. 2008, 130, 17970-17976 10.1021/ja807803j
10. Yue, W.; Lv, A.; Gao, J.; Jiang, W.; Hao, L.; Li, C.; Li, Y.; Polander, L. E.; Barlow, S.; Hu, W.; Di Motta, S.; Negri, F.; Marder, S. R.; Wang, Z. J. Am. Chem. Soc. 2012, 134, 5770-5773 10.1021/ja301184r
11. Li, C.; Wonneberger, H. Adv. Mater. 2012, 24, 613-636 10.1002/adma.201104447
12. Nielsen, C. B.; Holliday, S.; Chen, H.-Y.; Cryer, S. J.; McCulloch, I. Acc. Chem. Res. 2015, 48, 2803-2812 10.1021/acs.accounts.5b00199
13. Hartnett, P. E.; Timalsina, A.; Ramakrishna Matte, H. S. S.; Zhou, N.; Guo, X.; Zhao, W.; Facchetti, A.; Chang, R. P. H.; Hersam, M. C.; Wasielewski, M. R.; Marks, T. J. J. Am. Chem. Soc. 2014, 136, 16345-16356 10.1021/ja508814z
14. Cai, Y.; Huo, L.; Sun, X.; Wei, D.; Tang, M.; Sun, Y. Adv. Energy Mater. 2015, 5, 1500032 10.1002/aenm.201500032
15. Rajaram, S.; Shivanna, R.; Kandappa, S. K.; Narayan, K. S. J. Phys. Chem. Lett. 2012, 3, 2405-2408 10.1021/jz301047d
16. Wu, C.-H.; Chueh, C.-C.; Xi, Y.-Y.; Zhong, H.-L.; Gao, G.-P.; Wang, Z.-H.; Pozzo, L. D.; Wen, T.-C.; Jen, A. K. Y. Adv. Funct. Mater. 2015, 25, 5326-5332 10.1002/adfm.201501971
17. Ye, L.; Sun, K.; Jiang, W.; Zhang, S.; Zhao, W.; Yao, H.; Wang, Z.; Hou, J. ACS Appl. Mater. Interfaces 2015, 7, 9274-9280 10.1021/acsami.5b02012
18. Yan, Q.; Zhou, Y.; Zheng, Y.-Q.; Pei, J.; Zhao, D. Chem. Sci. 2013, 4, 4389-4394 10.1039/c3sc51841h
19. Zhang, X.; Lu, Z.; Ye, L.; Zhan, C.; Hou, J.; Zhang, S.; Jiang, B.; Zhao, Y.; Huang, J.; Zhang, S.; Liu, Y.; Shi, Q.; Liu, Y.; Yao, J. Adv. Mater. 2013, 25, 5791-5797 10.1002/adma.201300897
20. Liu, Y.; Mu, C.; Jiang, K.; Zhao, J.; Li, Y.; Zhang, L.; Li, Z.; Lai, J. Y. L.; Hu, H.; Ma, T.; Hu, R.; Yu, D.; Huang, X.; Tang, B. Z.; Yan, H. Adv. Mater. 2015, 27, 1015-1020 10.1002/adma.201404152
21. Meng, D.; Sun, D.; Zhong, C.; Liu, T.; Fan, B.; Huo, L.; Li, Y.; Jiang, W.; Choi, H.; Kim, T.; Kim, J. Y.; Sun, Y.; Wang, Z.; Heeger, A. J. J. Am. Chem. Soc. 2016, 138, 375-380 10.1021/jacs.5b11149
22. Sun, D.; Meng, D.; Cai, Y.; Fan, B.; Li, Y.; Jiang, W.; Huo, L.; Sun, Y.; Wang, Z. J. Am. Chem. Soc. 2015, 137, 11156-11162 10.1021/jacs.5b06414
23. Zhong, H.; Wu, C.-H.; Li, C.-Z.; Carpenter, J.; Chueh, C.-C.; Chen, J.-Y.; Ade, H.; Jen, A. K.-Y. Adv. Mater. 2016, 28, 951-958 10.1002/adma.201504120
24. Hartnett, P. E.; Ramakrishna Matte, H. S. S.; Eastham, N. D.; Jackson, N. E.; Wu, Y.; Chen, L. X.; Ratner, M. A.; Chang, R. P. H.; Hersam, M. C.; Wasielewski, M. R.; Marks, T. J. Chem. Sci. 2016, 7, 3543-3555 10.1039/C5SC04956C
25. Yue, W.; Gao, J.; Li, Y.; Jiang, W.; Di Motta, S.; Negri, F.; Wang, Z. J. Am. Chem. Soc. 2011, 133, 18054-18057 10.1021/ja207630a
26. Gao, J.; Li, Y.; Wang, Z. Org. Lett. 2013, 15, 1366-1369 10.1021/ol400324w
27. Li, C.; Xiao, C.; Li, Y.; Wang, Z. Org. Lett. 2013, 15, 682-685 10.1021/ol303551p
28. Li, C.; Lin, Z.; Li, Y.; Wang, Z. Chem. Rec. 2016, 16, 873-885 10.1002/tcr.201500246
29. Li, Y.; Xu, W.; Di Motta, S.; Negri, F.; Zhu, D.; Wang, Z. Chem. Commun. 2012, 48, 8204-8206 10.1039/c2cc33529h
30. Li, Y.; Wang, C.; Li, C.; Di Motta, S.; Negri, F.; Wang, Z. Org. Lett. 2012, 14, 5278-5281 10.1021/ol302434y
31. Zhong, Y.; Trinh, M. T.; Chen, R.; Purdum, G. E.; Khlyabich, P. P.; Sezen, M.; Oh, S.; Zhu, H.; Fowler, B.; Zhang, B.; Wang, W.; Nam, C.-Y.; Sfeir, M. Y.; Black, C. T.; Steigerwald, M. L.; Loo, Y.-L.; Ng, F.; Zhu, X.-Y.; Nuckolls, C. Nat. Commun. 2015, 6, 8242 10.1038/ncomms9242
32. Zhong, Y.; Kumar, B.; Oh, S.; Trinh, M. T.; Wu, Y.; Elbert, K.; Li, P.; Zhu, X.; Xiao, S.; Ng, F.; Steigerwald, M. L.; Nuckolls, C. J. Am. Chem. Soc. 2014, 136, 8122-8130 10.1021/ja503533y
33. Li, Y.; Tan, L.; Wang, Z.; Qian, H.; Shi, Y.; Hu, W. Org. Lett. 2008, 10, 529-532 10.1021/ol703046w
34. Li, Y.; Li, C.; Yue, W.; Jiang, W.; Kopecek, R.; Qu, J.; Wang, Z. Org. Lett. 2010, 12, 2374-2377 10.1021/ol1007197
35. Liu, C.; Xiao, C.; Li, Y.; Hu, W.; Li, Z.; Wang, Z. Chem. Commun. 2014, 50, 12462-12464 10.1039/C4CC05896H
36. Jiang, L.; Gao, J.; Wang, E.; Li, H.; Wang, Z.; Hu, W.; Jiang, L. Adv. Mater. 2008, 20, 2735-2740 10.1002/adma.200800341
37. Huo, L.; Liu, T.; Sun, X.; Cai, Y.; Heeger, A. J.; Sun, Y. Adv. Mater. 2015, 27, 2938-2944 10.1002/adma.201500647
38. Malliaras, G. G.; Salem, J. R.; Brock, P. J.; Scott, C. Phys. Rev. B: Condens. Matter Mater. Phys. 1998, 58, R13411 10.1103/PhysRevB.58.R13411