Synthesis and optical properties of perylene diimide derivatives with triphenylene-based dendrons linked at the bay positions through a conjugated ethynyl linkage

Tetrahedron

Volumn 68, Issue 13, 2012, Pages 2806-2818

  Bagui, Mahuya ^a   Dutta, Tanmoy ^a   Zhong, Haizhen ^b   Li, Shaohua ^a   Chakraborty, Sanjiban ^a   Keightley, Andrew ^a   Peng, Zhonghua ^a  

^a UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

^b UNIVERSITY OF NEBRASKA AT OMAHA   (United States)

Author keywords

Charge transfer; Dendrimer; Perylenediimide; Triphenylene

Indexed keywords

ACETYLENE; ALKYNYL GROUP; BENZENE DERIVATIVE; IMIDE; PERYLENE; SOLVENT;

ARTICLE; CONJUGATION; DILUTION; ELECTRON TRANSPORT; FILM; FLUORESCENCE; OPTICAL ROTATION; PHOTOCHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 84862785758     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.02.008     Document Type: Article

References (67)

1. P. Gawrys, D. Boudinet, M. Zagorska, D. Djurado, J. Verilhac, G. Horowitz, J. Pecaud, S. Pouget, and A. Pron Synth. Met. 159 2009 1478
2. T. Weil, E. Reuther, and K. Müllen Angew. Chem., Int. Ed. 41 2002 1900
3. J.M. Serin, D.W. Brousmiche, and J.M.J. Fréchet Chem. Commun. 2002 2605
4. A. Sautter, B.K. Kaletas, D.G. Schmid, R. Dobrawa, M. Zimine, G. Jung, I.H.M. van Stokkum, L.D. Cola, R.M. Williams, and F. Würther J. Am. Chem. Soc. 127 2005 6719
5. S.K. Lee, Y. Zu, A. Herrmann, Y. Geerts, K. Müllen, and A.J. Bard J. Am. Chem. Soc. 121 1999 3513
6. H. Yan, Z. Chen, Y. Zheng, C. Newman, J.R. Quinn, F. Dötz, M. Kastler, and A. Facchetti Nature 457 2009 679
7. B.A. Jones, M.J. Ahrens, M.H. Yoon, A. Facchetti, T.J. Marks, and M.R. Wasielewski Angew. Chem., Int. Ed. 43 2004 6363
8. Z. An, J. Yu, S.C. Jones, S. Barlow, S. Yoo, B. Domercq, P. Prins, L.D.A. Siebbeles, B. Kippelen, and S.R. Marder Adv. Mater. 17 2005 2580
9. K.Y. Law Chem. Rev. 93 1993 449
10. M.P. O'Neil, M.P. Niemczyk, W.A. Svec, D. Gosztola, G.L. Gaines III, and M.R. Wasielewski Science 257 1992 63
11. S. Prathapan, S.I. Yang, J. Seth, M.A. Miller, D.F. Bocian, D. Holten, and J.S. Lindsey J. Phys. Chem. B 105 2001 8237
12. C. Huang, S. Barlow, and S.R. Marder J. Org. Chem. 76 2011 2386
13. X. He, H. Liu, Y. Li, S. Wang, N. Wang, J. Xiao, X. Xu, and D. Zhu Adv. Mater. 17 2005 2811
14. B. Wang, and C. Yu Angew. Chem., Int. Ed. 49 2010 1485
15. Y. Che, X. Yang, G. Liu, C. Yu, H. Ji, J. Zuo, J. Zhao, and L. Zang J. Am. Chem. Soc. 132 2010 5743
16. Y. Che, A. Datar, X. Yang, T. Naddo, J. Zhao, and L. Zang J. Am. Chem. Soc. 129 2007 6354
17. Y. Huang, L. Fu, W. Zou, F. Zhang, and Z. Wei J. Phys. Chem. C 115 2011 10399
18. J.J. Dittmer, E.A. Marseglia, and R.H. Friend Adv. Mater 12 2000 l270
19. J. Roncali, P. Frre, P. Blanchard, R. Bettignies, M. Turbiez de, S. Roquet, P. Leriche, and Y. Nicolas Thin Solid Films 5l1/512 2006 567
20. J. Li, F. Dierschke, J. Wu, A.C. Grimsdale, and K. Mllen J. Mater. Chem. 16 2006 96
21. P. Jonkheijm, N. Stutzmann, Z. Chen, D.M. de Leeuw, E.W. Meijer, A.P.H.J. Schenning, and F. Wrthner J. Am. Chem. Soc. 128 2006 9535
22. E.E. Neuteboom, S.C.J. Meskers, P.A. van Hal, J.K.J. van Duren, E.W. Meijer, R.A.J. Janssen, H. Dupin, G. Pourtois, J. Cornil, R. Lazzaroni, J.-L. Brédas, and D. Beljonne J. Am. Chem. Soc. 125 2003 8625
23. C. Li, M. Liu, N.G. Pschirer, M. Baumgarten, and K. Mullen Chem. Rev. 110 2010 6817
24. L. Schmidt-Mende, A. Fechtenkötter, K. Müllen, E. Moons, R.H. Friend, and J.D. MacKenzie Science 293 2001 1119
25. X. Zhan, Z.A. Tan, B. Domercq, Z. An, X. Zhang, S. Barlow, Y. Li, D. Zhu, B. Kippelen, and S.R. Marder J. Am. Chem. Soc. 129 2007 7246
26. F. Würthner Chem. Commun. 2004 1564
27. L. Zang, Y. Che, and J.S. Moore Acc. Chem. Res. 41 2008 1596
28. M.R. Wasielewski J. Org. Chem. 71 2006 5051
29. Y. Li, L. Tan, Z. Wang, H. Qian, Y. Shi, and W. Hu Org. Lett. 10 2008 529
30. C.L. Zhan, and A.D.Q. Li Curr. Org. Chem. 15 2011 1314
31. D. Ke, C. Zhan, S. Xu, X. Ding, A. Peng, J. Sun, S. He, A.D.Q. Li, and J. Yao J. Am. Chem. Soc. 2011 ASAP
32. Z. Chen, M.G. Debije, T. Debaerdemaeker, P. Osswald, and F. Wrthner ChemPhysChem 5 2004 137
33. W. Wang, A.D. Shaller, and A.D.Q. Li J. Am. Chem. Soc. 130 2008 8271
34. R. Schmidt, J.H. Oh, Y.-S. Sun, M. Deppisch, A.-M. Krause, K. Radacki, H. Braunschweig, M. Knemann, P. Erk, Z. Bao, and F. Wrthner J. Am. Chem. Soc. 131 2009 6215
35. M.L. Tang, J.H. Oh, A.D. Reichardt, and Z. Bao J. Am. Chem. Soc. 131 2009 3733
36. R. Schmidt, M.M. Ling, J.H. Oh, M. Winkler, M. Konemann, Z. Bao, and F. Wurthner Adv. Mater. 19 2007 3692
37. M.C.R. Delgado, E.-G. Kim, D.A. da Silva Filho, and J.-L. Bredas J. Am. Chem. Soc. 132 2010 3375
38. R.T. Weitz, K. Amsharov, U. Zschieschang, E.B. Villas, D.K. Goswami, M. Burghard, H. Dosch, M. Jansen, K. Kern, and H. Klauk J. Am. Chem. Soc. 130 2008 4637
39. A.S. Molinari, H. Alves, Z. Chen, A. Facchetti, and A.F. Morpurgo J. Am. Chem. Soc. 131 2009 2462
40. M.H. Yoon, A. Facchetti, C.E. Stern, and T.J. Marks J. Am. Chem. Soc. 128 2006 5792
41. R.K. Dubey, A. Efimov, and H. Lemmetyinen Chem. Mater. 23 2010 778
42. C.-C. Chao, M.-k. Leung, Y.O. Su, K.-Y. Chiu, T.-H. Lin, S.-J. Shieh, and S.-C. Lin J. Org. Chem. 70 2005 4323
43. S. Chen, Y. Liu, W. Qiu, X. Sun, Y. Ma, and D. Zhu Chem. Mater. 17 2005 2208
44. J. Huang, H. Fu, Y. Wu, S. Chen, F. Shen, X. Zhao, Y. Liu, and J. Yao J. Phys. Chem. C 112 2008 2689
45. J. Huang, Y. Wu, H. Fu, X. Zhan, J. Yao, S. Barlow, and S.R. Marder J. Phys. Chem. A 113 2009 5039
46. M.J. Ahrens, L.E. Sinks, B. Rybtchinski, W. Liu, B.A. Jones, J.M. Giaimo, A.V. Gusev, A.J. Goshe, D.M. Tiede, and M.R. Wasielewski J. Am. Chem. Soc. 126 2004 8284
47. H. Qian, F. Negri, C. Wang, and Z. Wang J. Am. Chem. Soc. 130 2008 17970
48. B.C. Popere, A.M. Della Pelle, and S. Thayumanavan Macromolecules 44 2011 4767
49. G. Balaji, T.S. Kale, A. Keerthi, A.M. Della Pelle, S. Thayumanavan, and S. Valiyaveettil Org. Lett. 13 2010 18
50. N. Fabian, P. Wojciech, M. Sibylle, K. Christopher, and K. Müllen Chem. Mater. 18 2006 3715
51. Q. Yan, and D. Zhao Org. Lett. 11 2009 3426
52. S.A. Odom, F.K. Richard, S. Ohira, R. Trenton, T.R. Ensley, C. Huang, A. Lazaro, L.A. Padilha, S. Webster, V. Coropceanu, S. Barlow, D.J. Hagan, E.W.V. Stryland, J.-L. Brdas, H.A. Anderson, M.R. Wasielewski, and S.R. Marder J. Phys. Chem. A 113 2009 10826
53. R.F. Kelley, S.S. Won, B. Rybtchinski, E.L. Sinks, and M.R. Wasielewski J. Am. Chem. Soc. 129 2007 3173
54. A.J. Jiménez, S. Fabian, M.S. Rodríguez-Morgade, K. Ohkubo, S. Fukuzumi, D.M. Guldi, and T. Torres Org. Lett. 9 2007 2481
55. Z. An, A.O. Susan, R.F. Kelley, C. Huang, X. Zhang, S. Barlow, L.A. Padilha, J. Fu, S. Webster, D.J. Hagan, E.W.V.S. Stryland, M.R. Wasielewski, and S.R. Marder J. Phys. Chem. A 113 2009 5585
56. A.E. Clark, C. Qin, and A.D.Q. Li J. Am. Chem. Soc. 129 2007 7586
57. F. Wuerthner, V. Stepanenko, Z. Chen, C.R. Saha-Moeller, N. Kocher, and D. Stalke J. Org. Chem. 69 2004 7933
58. M. Bagui, T. Dutta, S. Chakraborty, J.S. Melinger, H. Zhong, A. Keightley, and Z. Peng J. Phys. Chem. A 115 2011 1579
59. M. Bagui, J. Melinger, S. Chakraborty, A.J. Keightley, and Z. Peng Tetrahedron 65 2009 1247
60. R. Gómez, D. Veldman, R. Blanco, C. Seoane, J.L. Segura, and R.A. Janssen Macromolecules 40 2007 2760
61. D.A. Case, D.A. Darden, T.E. Cheatham III, C.L. Simmerling, J. Wang, R.E. Duke, R. Luo, M. Crowley, R.C. Walker, W. Zhang, K.M. Merz, B. Wang, S. Hayik, A. Roitberg, G. Seabra, I. Kolossvary, K.F. Wong, F. Paesani, J. Vanicek, X. Wu, S.R. Brozell, T. Steinbrecher, H. Gohlke, L. Yang, J. Mongan, V. Hornak, and P.A. Kollman AMBER10 2008 University of California San Francisco
62. V. Hornak, R. Abel, A. Okur, B. Strockbine, A. Roitberg, and C.L. Simmerling Proteins 65 2006 712
63. The Molecular Operating Environment (MOE) 2010 Chemical Computing Group Montreal, Quebeck, Canada
64. The Cambridge Structural Database. http://www.ccdc.cam.ac.uk.
65. H. Zhong, and H.A. Carlson Proteins 58 2005 222
66. J.M. Serin, D.W. Brousmiche, and J.M.J. Fréchet J. Am. Chem. Soc. 124 2002 11848
67. Y. Liu, Y. Li, L. Jiang, H. Gan, H. Liu, Y. Li, J. Zhuang, F. Lu, and D. Zhu J. Org. Chem. 69 2004 9049