Contorted Tetrabenzocoronene Derivatives for Single Crystal Field Effect Transistors: Correlation between Packing and Mobility

Someshwar Pola; Chi-Hsien Kuo; Wei-Tao Peng; Md. Minarul Islam; Ito Chao; Yu-Tai Tao

doi:10.1021/cm301190c

journal article·2012-07-10

Contorted Tetrabenzocoronene Derivatives for Single Crystal Field Effect Transistors: Correlation between Packing and Mobility

Someshwar Pola, Chi-Hsien Kuo, Wei-Tao Peng, Md. Minarul Islam, Ito Chao, Yu-Tai Tao

Chemistry of Materials· Volume 24· Issue 13

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Source abstract

Abstract

A series of contorted tetrabenzo[a,d,j,m]coronenes (TBCs) substituted with four fluoro-, chloro-, or methyl groups at 2,7,12,17-positions were synthesized and characterized. Except for the one with methyl substituents, which exhibits a shifted π–π stacking, the rest all show cofacial π–π stacking with small parallel displacements. One-dimensional growth along the stacking direction was observed in the single crystals for all derivatives. A systematic comparison of the crystal packing and the calculated electronic coupling/mobility with the measured field-effect mobility for single-crystal field-effect transistors shows a good correlation.

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Research context

Electronic materials

OpenAlex topics: Organic Electronics and Photovoltaics · Organic and Molecular Conductors Research · Perovskite Materials and Applications

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan

References (55)

Show source-provided references

1. Gelinck G. · Adv. Mater. · 2010 · 22 · 377810.1002/adma.200903559 ↗

2. Muccini M. · Nat. Mater. · 2006 · 5 · 60510.1038/nmat1699 ↗

3. Dimitrakopoulos C. D. · Adv. Mater. · 2002 · 14 · 9910.1002/1521-4095(20020116)14:2<99::AID-ADMA99>3.0.CO;2-9 ↗

4. Dong H. · Chem. Commun. · 2010 · 46 · 521110.1039/c0cc00947d ↗

5. Klauk H. · Chem. Soc. Rev. · 2010 · 39 · 264310.1039/b909902f ↗

6. Murphy A. R. · Chem. Rev. · 2007 · 107 · 106610.1021/cr0501386 ↗

7. Roberts M. E. · J. Mater. Chem. · 2009 · 19 · 335110.1039/b816386c ↗

8. Di C. A. · Acc. Chem. Res. · 2009 · 42 · 1574

9. Jiang L. · J. Mater. Chem. · 2010 · 20 · 499410.1039/b925875b ↗

10. Reese C. · J. Mater. Chem. · 2006 · 16 · 32910.1039/B509636G ↗

11. de Boer R. W. I. · Phys. Status Solidi A · 2004 · 201 · 130210.1002/pssa.200404336 ↗

12. Gershenson M. E. · Rev. Mod. Phys. · 2006 · 78 · 97310.1103/RevModPhys.78.973 ↗

13. Takeya J. · J. Appl. Phys. · 2003 · 94 · 580010.1063/1.1618919 ↗

14. de Boer R.W. I. · Appl. Phys. Lett. · 2003 · 83 · 434510.1063/1.1629144 ↗

15. Islam M. M. · ACS Appl. Mater. Interfaces · 2011 · 3 · 213610.1021/am200349j ↗

16. Sundar V. C. · Science · 2004 · 303 · 164410.1126/science.1094196 ↗

17. Takeya J. · Appl. Phys. Lett. · 2007 · 90 · 10212010.1063/1.2711393 ↗

18. Coropceanu V. · Chem. Rev. · 2007 · 107 · 92610.1021/cr050140x ↗

19. Kwon O. · J. Chem. Phys. · 2004 · 120 · 818610.1063/1.1689636 ↗

20. Anslyn, E. A.; Dougherty, D. A.Modern Physical Organic Chemistry;University Science Books:Sausalito, CA, 2005; p19.

21. Anthony J. E. · J. Am. Chem. Soc. · 2001 · 123 · 948210.1021/ja0162459 ↗

22. Anthony J. E. · Org. Lett. · 2002 · 4 · 1510.1021/ol0167356 ↗

23. Xiao S. · Angew. Chem., Int. Ed. · 2005 · 44 · 739010.1002/anie.200502142 ↗

24. Oonishi I. · Bull. Chem. Soc. Jpn. · 1986 · 59 · 223310.1246/bcsj.59.2233 ↗

25. Fujisawa S. · Bull. Chem. Soc. Jpn. · 1982 · 55 · 342410.1246/bcsj.55.3424 ↗

26. Islam Md. M. · Chem. Commun. · 2011 · 47 · 200810.1039/C0CC04773B ↗

27. Zhang X. · J. Org. Chem. · 2010 · 75 · 806910.1021/jo101701k ↗

28. Podzorov V. · Appl. Phys. Lett. · 2003 · 82 · 173910.1063/1.1560869 ↗

29. Sze, S. M.Semiconductor Device Physics and Technology,2nd ed.Wiley:New York, 2001; Chapter 6, p169.

30. Kuo M.-Y. · Chem.—Eur. J. · 2007 · 13 · 475010.1002/chem.200601803 ↗

31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J.Gaussian 09, revision A.1;Gaussian, Inc.:Wallingford, CT, 2009.

32. Gruhn N. E. · J. Am. Chem. Soc. · 2002 · 124 · 791810.1021/ja0175892 ↗

33. Malagoli M. · J. Phys. Chem. · 2004 · 120 · 749010.1063/1.1687675 ↗

34. Chang Y.-C. · J. Phys. Chem. Lett. · 2010 · 1 · 11610.1021/jz900042x ↗

35. te Velde G. · J. Comput. Chem. · 2001 · 22 · 93110.1002/jcc.1056 ↗

36. Senthilkumar K. · J. Chem. Phys. · 2003 · 119 · 980910.1063/1.1615476 ↗

37. Prins P. · J. Phys. Chem. B · 2005 · 109 · 1826710.1021/jp053017i ↗

38. Sokolov A. N. · Nat. Comm. · 2011 · 2 · 43710.1038/ncomms1451 ↗

39. Stehr V. · Phys. Rev. B · 2011 · 83 · 15520810.1103/PhysRevB.83.155208 ↗

40. Song Y. · J. Am. Chem. Soc. · 2006 · 128 · 1594010.1021/ja064726s ↗

41. Deng W. Q. · J. Phys. Chem. B · 2004 · 108 · 861410.1021/jp0495848 ↗

42. Li H. · J. Chem. Phys. · 2007 · 126 · 16470410.1063/1.2727480 ↗

43. Koh S. E. · Adv. Funct. Mater. · 2008 · 18 · 33210.1002/adfm.200700713 ↗

44. Plunkett K. N. · Org. Lett. · 2009 · 11 · 222510.1021/ol9001834 ↗

45. Loo Y. L. · Ort. Lett. · 2010 · 12 · 4841

46. Clar E. · Tetrahedron · 1972 · 28 · 113710.1016/0040-4020(72)80174-1 ↗

47. Donovan P. M. · J. Am. Chem. Soc. · 2004 · 126 · 310810.1021/ja038254i ↗

48. Miyaura N. · Chem. Rev. · 1995 · 95 · 245710.1021/cr00039a007 ↗

49. Navale T. S. · Org. Lett. · 2011 · 13 · 163410.1021/ol200069c ↗

50. Plunkett K. N. · Org. Lett. · 2009 · 11 · 222510.1021/ol9001834 ↗

51. Wei Z. · Adv. Mater. · 2010 · 22 · 245810.1002/adma.201000088 ↗

52. Sanchez-Carrera R. S. · J. Phys. Chem. C · 2010 · 114 · 233410.1021/jp910102f ↗

53. Zhu L. · J. Phys. Chem. C · 2010 · 114 · 2040110.1021/jp104061c ↗

54. Chen H.-Y. · Chem. Phys. Lett. · 2005 · 401 · 53910.1016/j.cplett.2004.11.125 ↗

55. Chen H.-Y. · ChemPhysChem · 2006 · 7 · 200310.1002/cphc.200600266 ↗