Crystallization-induced properties from morphology-controlled organic crystals

Accounts of Chemical Research

Volumn 47, Issue 8, 2014, Pages 2353-2364

  Park, Chibeom ^a   Park, Ji Eun ^a   Choi, Hee Cheul ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84906237550     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar5000874     Document Type: Article

References (45)

1. Babu, S. S.; Möhwald, H.; Nakanishi, T. Recent progress in morphology control of supramolecular fullerene assemblies and its applications Chem. Soc. Rev. 2010, 39, 4021-4035
2. Shrestha, L. K.; Ji, Q.; Mori, T.; Miyazawa, K.; Yamauchi, Y.; Hill, J. P.; Ariga, K. Fullerene nanoarchitectonics: from zero to higher dimensions Chem.-Asian J. 2013, 8, 1662-1679
3. 60 disks on graphite substrate by a vapor-solid process Angew. Chem., Int. Ed. 2008, 47, 693-696
4. 60) self-Assembly into dot, wire and disk structures Chem. Commun. 2009, 4803-4805
5. 60 nanowires by solvent vapor annealing process ACS Nano 2013, 7, 9122-9128
6. 70 cubes and remarkable enhancement of photoluminescence Angew. Chem., Int. Ed. 2010, 49, 9670-9675
7. 16CuPc) ribbon Chem. Commun. 2010, 46, 231-233
8. Moon, H. K.; Son, M.; Park, J. E.; Yoon, S. M.; Lee, S. H.; Choi, H. C. Significant increase in the water dispersibility of zinc phthalocyanine nanowires and applications in cancer phototherapy NPG Asia Mater. 2012, 4, e12
9. Tang, Q.; Li, H.; He, M.; Hu, W.; Liu, C.; Chen, K.; Wang, C.; Liu, Y.; Zhu, D. Low threshold voltage transistors based on individual single-crystalline submicrometer-sized ribbons of copper phthalocyanine Adv. Mater. 2006, 18, 65-68
10. Tong, W. Y.; Djurišić, A. B.; Xie, M. H.; Ng, A. C. M.; Cheung, K. Y.; Chan, W. K.; Leung, Y. H.; Lin, H. W.; Gwo, S. Metal phthalocyanine nanoribbons and nanowires J. Phys. Chem. B 2006, 110, 17406-17413
11. Park, J. E.; Son, M.; Hong, M.; Lee, G.; Choi, H. C. Crystal-plane- dependent photoluminescence of pentacene 1D wire and 2D disk crystals Angew. Chem., Int. Ed. 2012, 51, 6383-6388
12. Liu, H.; Li, Y.; Xiao, S.; Gan, H.; Jiu, T.; Li, H.; Jiang, L.; Zhu, D.; Yu, D.; Xiang, B.; Chen, Y. Synthesis of organic one-dimensional nanomaterials by solid-phase reaction J. Am. Chem. Soc. 2003, 125, 10794-10795
13. Wu, J. H.; Xu, T. Z.; Ang, S. G.; Xu, Q.-H.; Xu, G. Q. Radially oriented anthracene nanowire arrays: preparation, growth mechanism, and optical fluorescence Nanoscale 2011, 3, 1855-1860
14. Mei, J.; Diao, Y.; Appleton, A. L.; Fang, L.; Bao, Z. Integrated materials design of organic semiconductors for field-effect transistors J. Am. Chem. Soc. 2013, 135, 6724-6746
15. McQuarrie, D. A.; Simon, J. D. Physical Chemistry: A Molecular Approach; University Science Books: Sausalito, CA, 1997; pp 495-545.
16. Loi, M. A.; Como, E. D.; Dinelli, F.; Murgia, M.; Zamboni, R.; Biscarini, F.; Muccini, M. Supramolecular organization in ultra-thin films of α-sexithiophene on silicon dioxide Nat. Mater. 2005, 4, 81-85
17. Mattox, D. M. Handbook of Physical Vapor Deposition (PVD) Processing, 2 nd ed.; Elsevier Science: Oxford, 2010; pp 195-235.
18. Briseno, A. L.; Mannsfeld, S. C. B.; Ling, M. M.; Liu, S.; Tseng, R. J.; Reese, C.; Roberts, M. E.; Yang, Y.; Wudl, F.; Bao, Z. Patterning organic single-crystal transistor arrays Nature 2006, 444, 913-917
19. Sree Harsha, K. S. Principles of Physical Vapor Deposition of Thin Films, 1 st ed.; Elsevier Science: Oxford, 2005; pp 453-533.
20. Laudise, R. A.; Kloc, C.; Simpkins, P. G.; Siegrist, T. Physical vapor growth of organic semiconductors J. Cryst. Growth 1998, 187, 449-454
21. Kim, F. S.; Ren, G.; Jenekhe, S. A. One-dimensional nanostructures of π-conjugated molecular systems: assembly, properties, and applications from photovoltaics, sensors, and nanophotonics to nanoelectronics Chem. Mater. 2011, 23, 682-732
22. Reese, C.; Bao, Z. Organic single-crystal field-effect transistors Mater. Today 2007, 10, 20-27
23. Yoon, S. M.; Song, H. J.; Choi, H. C. p-Type semiconducting GeSe combs by a vaporization-condensation-recrystallization (VCR) process Adv. Mater. 2010, 22, 2164-2167
24. Yoon, S. M.; Hwang, I.-C.; Shin, N.; Ahn, D.; Lee, S. J.; Lee, J. Y.; Choi, H. C. Vaporization-condensation-recrystallization process-mediated synthesis of helical m -Aminobenzoic acid nanobelts Langmuir 2007, 23, 11875-11882
25. Yoon, S. M.; Hwang, I.-C.; Kim, K. S.; Choi, H. C. Synthesis of single-crystal tetra(4-pyridyl)porphyrin rectangular nanotubes in the vapor phase Angew. Chem., Int. Ed. 2009, 48, 2506-2509
26. Lee, M.; Park, J. E.; Park, C.; Choi, H. C. Synthesis of a p-type semiconducting phenothiazine exfoliatable layered crystal Langmuir 2013, 29, 9967-9971
27. Kolb, H. C.; Sharpless, K. B. The growing impact of click chemistry on drug discovery Drug Discovery Today 2003, 8, 1128-1137
28. Northrup, J. E.; Tiago, M. L.; Louie, S. G. Surface energetics and growth of pentacene Phys. Rev. B 2002, 66, 121404
29. 70 by alkali-metal doping Nature 1991, 350, 320-322
30. 60 close to the Mott transition Nature 2010, 466, 221-225
31. 3- phases-synthesis, structure, and electronic properties J. Am. Chem. Soc. 2002, 124, 5570-5580
32. 60 with iodine Nature 1992, 355, 712-714
33. Pekker, S.; Kováts, é.; Oszlányi, G.; Bényei, G.; Klupp, G.; Bortel, G.; Jalsovszky, I.; Jakab, E.; Borondics, F.; Kamarás, K.; Bokor, M.; Kriza, G.; Tompa, K.; Faigel, G. Rotor-stator molecular crystals of fullerenes with cubane Nat. Mater. 2005, 4, 764-767
34. 60 nanorods using m -xylene as a shape controller Adv. Mater. 2006, 18, 1883-1888
35. 60) nanowires J. Am. Chem. Soc. 2008, 130, 2527-2534
36. 60) nanosheets at the liquid-liquid interface J. Am. Chem. Soc. 2007, 129, 13816-13817
37. Wei, L.; Yao, J.; Fu, H. Solvent-Assisted self-Assembly of fullerene into single-crystal ultrathin microribbons as highly sensitive UV-visible photodetectors ACS Nano 2013, 7, 7573-7582
38. 60 at 100 K and 20 K Cryst. Res. Technol. 1996, 31, 43-53
39. 4 solvate. A solid-state study Chem. Phys. Lett. 1993, 208, 259-262
40. Deegan, R. D.; Bakajin, O.; Dupont, T. F.; Huber, G.; Nagel, S. R.; Witten, T. A. Capillary flow as the cause of ring stains from dried liquid drops Nature 1997, 389, 827-829
41. 60 nanowhiskers formed by the liquid-liquid interfacial precipitation method J. Mater. Res. 2002, 17, 83-88
42. Yoon, S. M.; Lee, J.; Je, J. H.; Choi, H. C.; Yoon, M. Optical waveguiding and lasing action in porphyrin rectangular microtube with subwavelength wall thicknesses ACS Nano 2011, 5, 2923-2929
43. Hinoue, T.; Shigenoi, Y.; Sugino, M.; Mizobe, Y.; Hisaki, I.; Miyata, M.; Tohnai, N. Regulation of π-stacked anthracene arrangement for fluorescence modulation of organic solid from monomer to excited oligomer emission Chem.-Eur. J. 2012, 18, 4634-4643
44. Huang, L.; Liao, Q.; Shi, Q.; Fu, H.; Ma, J.; Yao, J. Rubrene micro-crystals from solution routes: their crystallography, morphology and optical properties J. Mater. Chem. 2010, 20, 159-166
45. Mattheus, C. C.; Dros, A. B.; Baas, J.; Meetsma, A.; de Boer, J. L.; Palstra, T. T. M. Polymorphism in pentacene Acta Crystallogr. 2001, C57, 939-941