Hydrogen-bonded organic semiconductor micro- and nanocrystals: From colloidal syntheses to (opto-)electronic devices

Journal of the American Chemical Society

Volumn 136, Issue 47, 2014, Pages 16522-16532

  Sytnyk, Mykhailo ^a   Głowacki, Eric Daniel ^a   Yakunin, Sergii ^a   Voss, Gundula ^a   Schöfberger, Wolfgang ^a,c   Kriegner, Dominik ^a   Stangl, Julian ^a   Trotta, Rinaldo ^a   Gollner, Claudia ^a   Tollabimazraehno, Sajjad ^a   Romanazzi, Giuseppe ^b   Bozkurt, Zeynep ^a   Havlicek, Marek ^a   Sariciftci, Niyazi Serdar ^a   Heiss, Wolfgang ^a  

^a JOHANNES KEPLER UNIVERSITY LINZ   (Austria)

^b POLITECNICO DI BARI   (Italy)

^c UNIVERSITY OF SOUTH BOHEMIA   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; HYDROGEN BONDS; INFRARED DEVICES; LIGANDS; LIGHT ABSORPTION; NANOWIRES; NEMATIC LIQUID CRYSTALS; NITROGEN COMPOUNDS; PIGMENTS; SEMICONDUCTOR DEVICES; THERMOELECTRIC EQUIPMENT;

ABSORPTION AND PHOTOLUMINESCENCE; ENVIRONMENTALLY FRIENDLY ALTERNATIVES; INORGANIC NANOCRYSTALS; NANOWIRE TRANSISTORS; ORGANIC NANOCRYSTALS; PHOTOINDUCED CHARGE TRANSFER; SEMICONDUCTING NANOCRYSTALS; SURFACE FUNCTIONALITIES;

NANOCRYSTALS;

AMINE; DYE; NANOCRYSTAL; PHTHALOCYANINE; PIGMENT; RIBOFLAVIN;

ABSORPTION; ARTICLE; CATALYSIS; COLLOID; CRYSTAL; CRYSTAL STRUCTURE; HYDROGEN BOND; LUMINESCENCE; PHOTOLUMINESCENCE; PRECIPITATION; SEMICONDUCTOR; SYNTHESIS;

EID: 84914128894     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5073965     Document Type: Article

References (72)

1. Herbst, W.; Hunger, K. General. In Industrial Organic Pigments, 3 rd ed.; WILEY-VCH: Weinheim, 2004; pp 1-179.
2. Głowacki, E. D.; Voss, G.; Sariciftci, N. S. Adv. Mater. 2013, 25, 6783
3. The annual production is reported in the Organization for Economic Cooperation and Development (OECD) Screening Information Data Set (SIDS), CAS no. 147-14-8.
4. Shakhnovich, A.; Belmont, J. Pigments for Inkjet Applications. The chemistry of Inkjet Inks; World Scientific Publishing Co.: Singapore, 2010; pp 101-122.
5. Irimia-Vladu, M.; Głowacki, E. D.; Troshin, P. A.; Schwabegger, G.; Leonat, L.; Susarova, D. K.; Krystal, O.; Ullah, M.; Kanbur, Y.; Bodea, M. A.; Razumov, V. F.; Sitter, H.; Bauer, S.; Sariciftci, N. S. Adv. Mater. 2012, 24, 375-380
6. Anokhin, D. V.; Leshanskaya, L. I.; Piryazev, A. A.; Susarova, D. K.; Dremova, N. N.; Shcheglov, E. V.; Ivanov, D. A.; Razumova, V. F.; Troshin, P. A. Chem. Commun. 2014, 50, 7639-7641
7. Yanagisawa, H.; Mizuguchi, J.; Aramaki, S.; Sakai, Y. Jpn. J. Appl. Phys. 2008, 47, 4728-4731
8. Głowacki, E. D.; Leonat, L.; Irimia-Vladu, M.; Schwödiauer, R.; Ullah, M.; Sitter, H.; Bauer, S.; Sariciftci, N. S. Appl. Phys. Lett. 2012, 101, 023305
9. Głowacki, E. D.; Irimia-Vladu, M.; Kaltenbrunner, M.; Gasiorowski, J.; White, M. S.; Monkowius, U.; Romanazzi, G.; Suranna, G. P.; Mastrorilli, P.; Sekitani, T.; Bauer, S.; Someya, T.; Torsi, L.; Sariciftci, N. S. Adv. Mater. 2013, 25, 1563-1569
10. Gregory, P. J. Porphyrins Phthalocyanines 2000, 4, 432-437
11. Law, K. Y. Chem. Rev. 1993, 93, 449-486
12. Grätzel, M. J. Photochem. Photobiol., A 2004, 164, 3-14
13. Hardin, B. E.; Hoke, E. T.; Armstrong, P. B.; Yum, J. H.; Comte, P.; Torres, T.; Frechet, J. M. J.; Nazeeruddin, M. K.; Grätzel, M.; McGehee, M. D. Nat. Photonics 2009, 3, 406-411
14. For a review see: Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99-117
15. Bao, Z.; Lovinger, A. J.; Dodabalapur, A. Appl. Phys. Lett. 1996, 69, 3066-3068
16. Zambounis, J. S.; Hao, Z.; Iqbal, A. Nature 1997, 388, 131-132
17. Schaedeli, U.; Zambounis, J. S.; Iqbal, A.; Hao, Z.; Dubas, H.; 1993, EP 0654711.
18. Chen, T. L.; Chen, J. J-A.; Catane, L.; Ma, B. Org. Electron. 2011, 12, 1126-1131
19. Głowacki, E. D.; Voss, G.; Demirak, K.; Havlicek, M.; Sünger, N.; Okur, A. C.; Monkowius, U.; Gasiorowski, J.; Leonat, L.; Sariciftci, N. S. Chem. Commun. 2013, 49, 6063-6065
20. Sugiyama, T.; Asahi, T.; Takeuchi, H.; Masuhara, H. Jpn. J. Appl. Phys. 2006, 45, 384-388
21. Asahi, T.; Sugiyama, T.; Masuhara, H. Acc. Chem. Res. 2008, 41, 1790-1798
22. Tamaki, Y.; Asahi, T.; Masuhara, H. J. Phys. Chem. A 2002, 106, 2135-2139
23. Haberkorn, H.; Franke, D.; Frechen, Th.; Goesele, W.; Rieger, J. J. Colloid Interface Sci. 2003, 259, 112-126
24. Wang, J.; Zhao, Y.; Zhang, J.; Zhang, J.; Yang, B.; Wang, Y.; Zhang, D.; You, H.; Ma, D. J. Phys. Chem. C 2007, 111, 9177-9183
25. Nitschke, C.; OFlaherty, S. M.; Kroell, M.; Blau, W. J. J. Phys. Chem. B 2004, 108, 1287-1295
26. Yu, W. W.; Wang, Y. A.; Peng, X. Chem. Mater. 2003, 15, 4300-4308
27. van Embden, J.; Mulvaney, P. Langmuir 2005, 21, 10226-10233
28. Murray, C. B.; Noms, D. J.; Bawendi, M. G. J. Am. Chem. Soc. 1993, 115, 8706-8715
29. Rawal, V. H.; Cava, M. P. Tetrahedron Lett. 1985, 26, 6141-6142
30. Ashworth, I. W.; Cox, B. G.; Meyrick, B. J. Org. Chem. 2010, 75, 8117-8125
31. Ouchi, H.; Saito, Y.; Yamamoto, Y.; Takahata, H. Org. Lett. 2002, 4, 585-587
32. Kim, J. M.; Kang, J. H.; Han, D. K.; Lee, C. W.; Ahn, K. D. Chem. Mater. 1998, 10, 2332-2334
33. Paulus, E. F.; Leusen, F. J. J.; Schmidt, M. U. CrystEngComm 2007, 9, 131-143
34. de Melo, J. S. S.; Rondao, R.; Burrows, H. D.; de Melo, M.; Navaratnam, S.; Edge, R.; Voss, G. ChemPhysChem 2006, 7, 2303-2311
35. Talapin, D. V.; Rogach, A. L.; Kornowski, A.; Haase, M.; Weller, H. Nano Lett. 2001, 1, 207-211
36. de Mello Donegá, C.; Liljeroth, P.; Vanmaekelbergh, D. Small 2005, 1, 1152-1162
37. Dabbousi, B. O.; Rodriguez-Viejo, J.; Mikulec, F. V.; Heine, J. R.; Mattoussi, H.; Ober, R.; Jensen, K. F.; Bawendi, M. G. J. Phys. Chem. B 1997, 101, 9463-9475
38. Wang, C.; Chen, D.; Chen, W.; Chen, S.; Ye, K.; Zhang, H.; Zhang, J.; Wang, Y. J. Mater. Chem. C 2013, 1, 5548-5556
39. Fukunaga, H.; Fedorov, D. G.; Chiba, M.; Nii, K.; Kitaura, K. J. Phys. Chem. A 2008, 112, 10887-10894
40. Erk, P.; Hengelsberg, H.; Haddow, M. F.; van Gelder, R. CrystEngComm 2004, 6, 474-483
41. Desiraju, G. R. J. Mol. Struct. 2003, 656, 5-15
42. Rossi, L.; Bongiovanni, G.; Lanzani, G.; Mura, A.; Borghesi, A.; Tubino, R.; Kalinowski, J. Adv. Mater. Opt. Electron. 1997, 7, 35-38
43. Yang, F.; Wilkinson, M.; Austin, E. J.; ÓDonnell, K. P. Phys. Rev. Lett. 1993, 70, 323-326
44. Kim, D. H.; Lu, N.; Ma, R.; Kim, Y. S.; Kim, R. H.; Wang, S.; Wu, J.; Won, S. M.; Tao, H.; Islam, A.; Yu, K. J.; Kim, T.; Chowdhury, R.; Ying, M.; Xu, L.; Li, M.; Chung, H. J.; Keum, H.; McCormick, M.; Liu, P.; Zhang, Y. W.; Omenetto, F. G.; Huang, Y.; Coleman, T.; Rogers, J. A. Science 2011, 333, 838-843
45. Hammock, M. L.; Chortos, A.; Tee, B. C. K.; Tok, J. B. H.; Bao, Z. Adv. Mater. 2013, 25, 5997-6038
46. Matousek, J. L.; Campbell, K. L. Vet. Dermatol. 2002, 13, 293-300
47. Honda, T.; Kojima, T.; Kobayashi, N.; Fukuzumi, S. Angew. Chem., Int. Ed. 2011, 50, 2725-2728
48. Krauss, T. N.; Barrena, E.; Lohmüller, T.; Spatz, J. P.; Dosch, H. Phys. Chem. Chem. Phys. 2011, 13, 5940-5944
49. 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. J. Phys. Chem. B 2006, 110, 17406-17413
50. Wang, F. X.; Liu, Y. D.; Pan, G. B. Mater. Lett. 2011, 65, 933-936
51. Tong, W. Y.; Djurišić, A. B.; Ng, A. M. C.; Chan, W. K. Thin Solid Films 2007, 515, 5270-5274
52. Xiao, K.; Li, R.; Tao, J.; Payzant, E. A.; Ivanov, I. N.; Puretzky, A. A.; Hu, W.; Geohegan, D. B. Adv. Funct. Mater. 2009, 19, 3776-3780
53. Pron, A.; Garys, P.; Zagorska, M.; Djurado, D.; Demadrille, R. Chem. Soc. Rev. 2010, 39, 2577-2632
54. Dong, H.; Fu, X.; Liu, J.; Wang, Z.; Hu, W. Adv. Mater. 2014, 25, 6158-6183
55. Klauk, H. Chem. Soc. Rev. 2010, 39, 2643-2666
56. Ito, Y.; Virkar, A. A.; Mannsfeld, S.; Oh, J. H.; Toney, M.; Locklin, J.; Bao, Z. J. Am. Chem. Soc. 2009, 131, 9396-9404
57. Gur, I.; Fromer, N. A.; Geier, M. L.; Alivisatos, A. P. Science 2005, 310, 462-465
58. Kamat, P. V. J. Phys. Chem. C 2008, 112, 18737-18753
59. Robel, I.; Subramanian, V.; Kuno, M.; Kamat, P. V. J. Am. Chem. Soc. 2006, 128, 2385-2393
60. Walter, M. G.; Rudine, A. B.; Wamser, C. C. J. Porphyrins Phthalocyanines 2010, 14, 759-792
61. Tomida, M.; Kusabayashi, S.; Yokoyama, M. Chem. Lett. 1985, 8, 1305-1308
62. Chen, J. J.; Chen, T. L.; Kim, B.; Poulsen, D. A.; Mynar, J. L.; Fréchet, J. M.; Ma, B. ACS Appl. Mater. Interfaces 2010, 2, 2679-86
63. Varotto, A.; Nam, C. Y.; Radivojevic, I.; Tomé, J. P. C.; Cavaleiro, J. A. S.; Black, C. T.; Drain, C. M. J. Am. Chem. Soc. 2010, 132, 2552-2554
64. Scharber, M. C.; Mühlbacher, D.; Koppe, M.; Denk, P.; Waldauf, C.; Heeger, A. J.; Brabec, C. J. Adv. Mater. 2006, 18, 789-794
65. Heeger, A. J. Adv. Mater. 2014, 26, 10-28
66. Soci, C.; Hwang, I. W.; Moses, D.; Zhu, Z.; Waller, D.; Gaudiana, R.; Brabec, C. J.; Heeger, A. J. Adv. Funct. Mater. 2007, 17, 632-636
67. Blankenship, R. E.; Molecular Mechanism of Photosynthesis, 2 nd ed.; Wiley Blackwell: Chichester, 2014; pp 111-131.
68. Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J.; Wudl, F. Science 1992, 258, 1474-1476
69. Eder, F.; Klauk, H.; Halik, M.; Zschieschang, U.; Schmid, G.; Dehm, C. Appl. Phys. Lett. 2004, 84, 2673-2675
70. Hunger, K. Rev. Prog. Color. 2005, 35, 76-89
71. Jaffe, E. E.; Matrick, H. J. Org. Chem. 1968, 83, 4004-4010
72. Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650-4657