Novel pyromellitic diimide-based macrocycle with a linear π-electronic system and bis(phenylethynyl)pyromellitic diimide: Syntheses, structures, photophysical properties, and redox characteristics

Journal of Organic Chemistry

Volumn 73, Issue 11, 2008, Pages 4063-4075

  Kato, Shin Ichiro ^a   Nonaka, Yasuhiro ^a   Shimasaki, Toshiaki ^a   Goto, Kenta ^a   Shinmyozu, Teruo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; AROMATIC HYDROCARBONS; BENZENE; BIOELECTRIC PHENOMENA; CALCIUM; CALCULATIONS; CHEMICAL BONDS; CHEMICAL PROPERTIES; CHEMICAL REACTIONS; COMPUTER NETWORKS; CRYSTALLOGRAPHY; CYCLIC VOLTAMMETRY; DIFFERENCE EQUATIONS; EIGENVALUES AND EIGENFUNCTIONS; ELECTRONICS ENGINEERING; ELECTROSTATICS; FIGHTER AIRCRAFT; FLUORESCENCE; LIGHT EMISSION; LINEAR EQUATIONS; LUMINESCENCE; MEASUREMENTS; MICROFLUIDICS; MINERALOGY; NANOSTRUCTURED MATERIALS; SYNTHESIS (CHEMICAL); VOLTAMMETRY; X RAY CRYSTALLOGRAPHY; X RAYS;

(DIACETOXYIODO) BENZENE; (PL) PROPERTIES; AMERICAN CHEMICAL SOCIETY (ACS); CHEMICAL EQUATIONS; CLATHRATES; CRYSTALLOGRAPHIC STUDIES; CYCLO CONDENSATION; DIMER STRUCTURES; DONOR ACCEPTOR (D A); ELECTRONIC SYSTEMS; ELECTRONIC SYSTEMS (ES); ELECTRONIC TRANSITIONS; ELECTROSTATIC INTERACTIONS; ELECTROSTATIC REPULSIONS; EXCIMER FLUORESCENCE; FLUORESCENCE PROPERTIES; MACROCYCLE; PHENYLACETYLENE (PA); PHENYLETHYNYL; PHOTO-PHYSICAL PROPERTIES; SOLID STATES; SONOGASHIRA COUPLING REACTIONS; SPECTRAL MEASUREMENTS; THEORETICAL CALCULATIONS; VOLTAMMETRY MEASUREMENTS; X RAY CRYSTALLOGRAPHY;

STRUCTURAL PROPERTIES;

IMIDE; MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; OXIDATION REDUCTION STATE; PHOTOCHEMISTRY; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 44949196878     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800283r     Document Type: Article

References (99)

1. Molecular Tubes and Capsules, Part 4. For Part 1-3, see refs 17a-c.
2. (a) Würthner, F. Chem. Commun. 2004, 1564-1579.
3. (b) Grimsdale, A. C.; Müllen, K. Angew. Chem., Int. Ed. 2005, 44, 5592-5629.
4. (c) Wasielewski, M. R. J. Org. Chem. 2006, 71, 5051-5066.
5. (d) Würthner, F. Pure Appl. Chem. 2006, 78, 2341-2350.
6. (a) Katz, H. E.; Lovinger, A. J.; Johnson, J.; Kloc, C.; Siegrist, T.; Li, W.; Lin, Y.-Y.; Dodabalapur, A. Nature 2000, 404, 478-481.
7. (b) Katz, H. E.; Johnson, J.; Lovinger, A. J.; Li, W. J. Am. Chem. Soc. 2000, 122, 7787-7792.
8. (c) Hizu, K.; Sekitani, T.; Someya, T.; Otsuki, J. Appl. Phys. Lett. 2007, 90, 093504.
9. (a) Jones, B. A.; Ahrens, M. J.; Yoon, M.-H.; Facchetti, A.; Marks, T. J.; Wasielewski, M. R. Angew. Chem., Int. Ed. 2004, 43, 6363-6366.
10. (b) Chesterfield, R. J.; Mckeen, J. C.; Newman, C. R.; Ewbank, P. C.; da Silva Filho, D. A.; Brédas, J.-L.; Miller, L. L.; Mann, K. R.; Frisbie, C. D. J. Phys. Chem. B 2004, 108, 19281-19292.
11. (c) Jung, T.; Yoo, B.; Wang, L.; Dodabalapur, A.; Jones, B. A.; Facchetti, A.; Wasielewski, M. R.; Marks, T. J Appl. Phys. Lett. 2006, 88, 183012(13).
12. (d) Yoo, B.; Madgavkar, A.; Jones, B. A.; Nadkarni, S.; Facchetti, A.; Dimmler, K.; Wasielewski, M. R.; Marks, T. J.; Dodabalapur, A. IEEE Electron Device Lett. 2006, 27, 737-739.
13. (e) Wang, Y.; Chen, Y.; Li, R.; Wang, S.; Su, W.; Ma, P.; Wasielewski, M. R.; Jiang, J. Langmuir 2007, 23, 5842-5863.
14. (a) Thalacker, C.; Röger, C.; Würthner, F. J. Org. Chem. 2006, 71, 8098-8105.
15. (b) Röger, C.; Würthner, F. J. Org. Chem. 2007, 72, 8070-8075.
16. For a review of catenanes and oligocatenanes, see: Raehm, L.; Hamilton, D. G.; Sanders, J. K. M. Synlett 2002, 1743-1761.
17. For [2]catenanes, see: (a) Hamilton, D. G.; Sanders, J. K. M.; Davies, J. E.; Clegg, W.; Teat, S. J. Chem. Commun. 1997, 897-898.
18. (b) Hamilton, D. G.; Davies, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620.
19. (c) Hamilton, D. G.; Feeder, N.; Prodi, L.; Teat, S. J.; Clegg, W.; Sanders, J. K. M. J. Am. Chem. Soc. 1998, 120, 1096-1097.
20. (d) Zhang, Q.; Hamilton, D. G.; Feeder, N.; Teat, S. J.; Goodman, J. M.; Sanders, J. K. M. New J. Chem. 1999, 23, 897-903.
21. (e) Hamilton, D. G.; Prodi, L.; Feeder, N.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1999, 1057-1065.
22. (f) Hamilton, D. G.; Montalti, M.; Prodi, L.; Fontani, M.; Zanello, P.; Sanders, J. K. M. Chem. Eur. J. 2000, 6, 608-617.
23. (g) Hansen, J. G.; Feeder, N.; Hamilton, D. G.; Gunter, M. J.; Becher, J.; Sanders, J. K. M. Org. Lett. 2000, 2, 449-452.
24. (h) Gunter, M. J.; Farquhar, S. M. Org. Biomol. Chem. 2003, 1, 3450-3457.
25. (i) Fallon, G. D.; Lee, M. A.-P.; Langford, S. J.; Nichols, P. J. Org. Lett. 2004, 6, 655-658.
26. (j) Kaiser, G.; Jarrosson, T.; Otto, S.; Ng, Y.-F.; Bond, A. D.; Sanders, J. K. M. Angew. Chem., Int. Ed. 2004, 43, 1959-1962.
27. For [2]rotaxanes, see: (a) Nakamura, Y.; Minami, S.; Iizuka, K.; Nishimura, J. Angew. Chem., Int. Ed. 2003, 42, 3158-3162.
28. (b) Wang, X-Z.; Li, X.-Q.; Shao, X.-B.; Zhao, X.; Deng, P.; Jiang, X.-K.; Li, Z.-T.; Chen, Y.-Q. Chem. Eur. J. 2003, 9, 2904-2913.
29. (c) Vignon, S. A.; Jarrosson, T.; Iijima, T.; Tseng, H.-R., Sanders, J. K. M.; Stoddart, J. F J. Am. Chem. Soc. 2004, 126, 9884-9885.
30. (d) Iijima, T.; Vignon, S. A.; Tseng, H.-R.; Jarrosson, T.; Sanders, J. K. M.; Marchioni, F.; Venturi, M.; Apostoli, E.; Balzani, V.; Stoddart, J. F. Chem. Eur. J. 2004, 10, 6375-6392.
31. (a) Lokey, R. S.; Iverson, B. L. Nature 1995, 375, 303-305.
32. (b) Nguyen, B. L.; Iverson, B. L. J. Am. Chem. Soc. 1999, 121, 2639-2640.
33. (c) Gabriel, G. J.; Iverson, B. L. J. Am. Chem. Soc. 2002, 124, 15174-15175.
34. (a) Colquhoun, H. M.; Zhu, Z.; Williams, D. J. Org. Lett. 2003, 5, 4353-4356.
35. (b) Colquhoun, H. M.; Zhu, Z. Angew. Chem., Int. Ed. 2004, 43, 5040-5045.
36. (a) Würthner, F.; Thalacker, C.; Diele, S.; Tschierske, C. Chem. Eur. J. 2001, 7, 2245-2253.
37. (b) Würthner, F.; Chen, Z.; Dehm, V.; Stepanenko, V. Chem. Commun. 2006, 1188-1190.
38. (a) Li, X.-Q.; Stepanenko, V.; Chen, Z.; Prins, P.; Siebbeles, L. D. A.; Würthner, F. Chem. Commun. 2006, 3871-3873.
39. (b) Mukhopadhyay, P.; Iwashita, Y.; Shirakawa, M.; Kawano, S.; Fujita, N.; Shinkai, S. Angew. Chem., Int. Ed. 2006, 45, 1592-1595.
40. For the recent examples, see: (a) Chen, Z.; Stepanenko, V.; Dehm, V.; Prins, P.; Siebbeles, L. D. A.; Seibt, J.; Marquetand, P.; Engel, V.; Würthner, F. Chem. Eur. J. 2007, 13, 436-449.
41. (b) Chen, Z.; Baumeister, U.; Tschierske, C.; Würthner, F. Chem. Eur. J. 2007, 13, 450-465.
42. For pyromellitic diimide-bassed molecular duplexes, see: (a) Zhou, Q.-Z.; Jiang, X.-K.; Shao, X.-B.; Chen, G.-J.; Jia, M.-X.; Li, Z.-T. Org. Lett. 2003, 5, 1955-1958.
43. (b) Zhou, Q.-Z.; Jia, M.-X.; Shao, X.-B.; Wu, L.-Z.; Jiang, X.-K.; Li, Z.-T.; Chen, G.-J. Tetrahedron 2005, 61, 7117-7124.
44. (a) Chen, G.; Lean, J. T.; Alcalá, M.; Mallouk, T. E. J. Org. Chem. 2001, 66, 3027-3034.
45. (b) Colquhoun, H. M.; Williams, D. J.; Zhu, Z. J. Am. Chem. Soc. 2002, 124, 13346-13347.
46. Fox et al. have most recently reported the synthesis of π-conjugated compounds based on pyromellitic diimide moiety, N,N′-di(2-tert- butylphenyl)3,6-di(4-chlorophneyl)pyromellitic diimide, by the approach different from ours. See: Dong, Z.; Liu, X.; Yap, G. P. A.; Fox, J. M. J. Org. Chem. 2007, 72, 617-625.
47. (a) Iwanaga, T.; Yasutake, M.; Takemura, H.; Sako, K.; Shinmyozu, T. Angew. Chem., Int. Ed. 2006, 45, 3643-3647.
48. (b) Kato, S.; Matsumoto, T.; Ideta, K.; Shimasaki, T.; Goto, K.; Shinmyozu, T. J. Org. Chem. 2006, 71, 4723-4733.
49. (c) Kato, S.; Nakagaki, T.; Shimasaki, T.; Shinmyozu, T. CrystEngComm In press.
50. (a) Stang, P. J.; Diederich, F., Eds. Modern Acetylene Chemistry; Wiley-VCH: Weinheim, 1995.
51. (b) de Meijere, A., Ed. Top. Curr. Chem. (Carbon Rich Compounds I); Springer: Berlin, Germany, 1998; Vol. 196.
52. (c) de Meijere, A., Ed. Top. Curr. Chem. (Carbon Rich Compounds I); Springer: Berlin, Germany, 1999; Vol. 201.
53. (d) Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds. Acetylene Chemistry: Chemistry, Biology, and Material Science; Wiley-VCH: Weinheim, Germany, 2005.
54. (e) Haley, M. M.; Tykwinski, R. R., Eds. Carbon-Rich Compounds: From Molecules to Materials; Wiley-VCH: Weinheim, Germany, 2006.
55. For recent reviews of aromatic acetylenes, see: (a) Diederich, F.; Gobbi, L. Top. Curr. Chem. 1999, 201, 43-79.
56. (b) Haley, M. M.; Pak, J. J.; Brand, S. C. Top. Curr. Chem. 1999, 201, 81-130.
57. (c) Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Chem. Soc. Rev. 1999, 101-119.
58. (d) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153-3180.
59. (e) Bunz, U. H. F. Chem. Rev. 2000, 100, 1605-1644.
60. (f) Tour, J. M. Acc. Chem. Res. 2000, 33, 791-804.
61. (g) Simsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632-2657.
62. (h) Diederich, F. Chem. Commun. 2001, 219-227.
63. (i) Zhao, D.; Moore, J. S. Chem. Commun. 2003, 807-818.
64. (j) Spitler, E. L.; Johnson, C. A.; Haley, M. M. Chem. Rev. 2006, 106, 5344-5386.
65. (k) Orita, A.; Otera, J. Chem. Rev. 2006, 106, 5387-5412.
66. Sasaki, S.; Mizuno, M.; Naemura, K.; Tobe, Y. J. Org. Chem. 2000, 65, 275-283.
67. (a) Mohr, B.; Enkelmann, V.; Wegner, G. J. Org. Chem. 1994, 59, 635-638.
68. (b) Higuchi, T.; Satake, C.; Hirobe, M. J. Am. Chem. Soc. 1995, 117, 8879-8880.
69. Suh, D. H.; Chung, E. Y.; Hong, Y.-T; Choi, K.-Y. Angew. Makromol. Chem. 1998, 254, 33-38.
70. 22 Thus, our procedure was described in the Experimental Section. The use of unpurified 9 significantly decreased the cyclocondensation yield (less than 1%) probably due to the side reactions.
71. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470.
72. (b) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49.
73. We also prepared the tetrabromide 12 with the dibutoxy substituents at the benzene linkers (Experimental Section) by the cyclocondensation of the anhydride 9 and 1,3-bis(aminomethyl)-4,6-di- n-butoxybenzene and attempted the Sonogashira reaction of 12 with phenylacetylene under the same reaction conditions for the synthesis of 2. However, the reaction resulted in the quantitative recovery of 12 due to the poor solubility of 12 in common organic solvents.
74. 2. The macrocycle 2 easily crystallized below 0°C and 10 did not dissolve in common organic solvents.
75. The standard van der Waals radii are taken from: Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
76. For review of high-accuracy quantum mechanical studies in benzene dimers, see: Sinnokrot, M. O.; Sherrill, C. D. J. Phys. Chem. A 2006, 110, 10656-10668.
77. In the optimized structure of 2′ at the B3LYP/6-31G* level, the transannular distance between the benzene rings of the diimide moieties is 5.17 Å: This value is clearly larger than the experimental value. It is pointed out that the underestimation of attractive π-π interaction is common to anthracene-acetylene oligomers at the B3LYP/6-31G level by Toyota et al, see: Ishikawa, T.; Shimasaki, T.; Akashi, H.; Toyota, S. Org. Lett. 2008, 10, 417-420.
78. 17b
79. The crystal packing of dehydro[12]annulene fused with tetrafluorobenzne, in which one of the tetrafluorobenzene rings faced the annulene core of another molecule, was rationalized with its Mulliken charge by using B3LYP/6-31G(d) level of theory by Komatsu et al., see: Nishinaga, T.; Nodera, N.; Miyata, Y.; Komatsu, K. J. Org. Chem. 2002, 67, 6091-6096.
80. 16
81. Nishio, M.; Hirota, M.; Umezawa, Y. The CH/π interactions; Wiley-VCH: New York, 1998.
82. Gawroński, J.; Brzostowska, M.; Gawrońska, K.; Koput, J.; Rychlewska, U.; Skowronek, P.; Nordén, B. Chem. Eur. J. 2002, 8, 2484-2494.
83. Buchwalter, S. L.; Iyengar, R.; Viehbeck, A.; O'Toole, T. R. J. Am. Chem. Soc. 1991, 113, 376-377.
84. Carroll, J. B.; Gray, M.; McMenimen, K. A.; Hamilton, D. G.; Rotello, V. M. Org. Lett. 2003, 5, 3177-3180.
85. (a) Benesi, H. A.; Hildebrand, J. J. J. Am. Chem. Soc. 1949, 71, 2703-2707.
86. (b) Person, W. B. J. Am. Chem. Soc. 1965, 87, 167-170.
87. Kishikawa, K.; Tsubokura, S.; Kohmoto, S.; Yamamoto, M.; Yamaguchi, K. J. Org. Chem. 1999, 64, 7568-7578.
88. For covalent organic nanotubes, see: (a) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518.
89. (b) Ikeda, A.; Shinkai, S. Chem. Commun. 1994, 2375-2376.
90. (c) Kammermeiter, S.; Herges, R. Angew. Chem., Int. Ed. 1996, 35, 2669-2671.
91. (d) Kim, S. K.; Sim, W.; Vicens, J.; Kim, J. S. Tetrahedron Lett. 2003, 44, 805-809.
92. (e) Kim, Y.; Mayer, M. F.; Zimmerman, S. C. Angew. Chem., Int. Ed. 2003, 42, 1121-1126.
93. (f) Organo, V. G.; Leontiev, A. V.; Sgarlata, V.; Dias, H. V. R.; Rudkevich, D. M. Angew. Chem., Int. Ed. 2005, 44, 3043-3047.
94. (g) Jin, W.; Fukushima, T.; Kosaka, A.; Niki, M.; Ishii, N.; Aida, T. J. Am. Chem. Soc. 2005, 127, 8284-8285.
95. (h) Organo, V. G.; Sgarlata, V.; Firouzbakht, F.; Rudkevich, D. M. Chem. Eur. J. 2007, 13, 4014-4023.
96. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; 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.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
97. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
98. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
99. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206.