Interplay between structural and dielectric features of new low k hybrid organic-organometallic supramolecular ribbons

Crystal Growth and Design

Volumn 12, Issue 1, 2012, Pages 297-305

  Sgarbossa, Paolo ^a   Bertani, Roberta ^a   Di Noto, Vito ^a   Piga, Matteo ^a   Giffin, Guinevere A ^a   Terraneo, Giancarlo ^b,c   Pilati, Tullio ^b   Metrangolo, Pierangelo ^b,c   Resnati, Giuseppe ^b,c  

^a UNIVERSITY OF PADOVA   (Italy)

^b POLITECNICO DI MILANO   (Italy)

^c ISTITUTO ITALIANO DI TECNOLOGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1D CHAIN; CHAIN MOBILITY; CHLOROFORM SOLUTIONS; CO-CRYSTALS; COCRYSTALLIZATION; CRYSTAL PACKINGS; DIELECTRIC PERMITTIVITIES; HALOGEN BONDS; ISOTHERMAL EVAPORATION; NON-COVALENT INTERACTION; PERMITTIVITY VALUES; REAL COMPONENTS; ROOM TEMPERATURE; TEMPERATURE RANGE; X-RAY STRUCTURE;

CHARACTERIZATION; CRYSTAL STRUCTURE; DIELECTRIC FILMS; ETHYLENE; MICROELECTRONICS; PERMITTIVITY; PLATINUM; SILICA; SILICON COMPOUNDS; SUPRAMOLECULAR CHEMISTRY;

ORGANOMETALLICS;

EID: 84855366156     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg201073m     Document Type: Article

References (101)

1. Saalfrank, R. W. and Demleitner, B. In Transition Metals in Supramolecular Chemistry; Sauvage, J. P., Ed.; Wiley & Sons: Chichester, 1999; Vol. 5, Chapter 1, pp 1-52.
2. Haiduc, I and Edilmann, F. T. Supramolecular Organometallic Chemistry; Wiley VCH: New York, 2000.
3. Batten, S. R., Neville, S. M., and Turner, D. R. Coordination Polymers. Design, Analysis and Applications; RCS Publishing: Cambridge, 2009.
4. Kurth, D. G. Sci. Technol. Adv. Mater. 2008, 9, 1-25
5. Corriu, R.; Mehdi, A.; Reyè, C. J. Organomet. Chem. 2004, 689, 4437-4450
6. Manciu, F.; Rampazzo, E.; Tecilla, P.; Tonellato, U. Chem.-Eur. J. 2006, 12, 1844-1854
7. Xia, Y.; Yang, P.; Sun, Y.; Wu, Y.; Mayers, B.; Gates, B.; Yin, Y.; Kim, F.; Han., H. Adv. Mater. 2003, 15, 353-389
8. Philp, D.; Stoddard, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196
9. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 2007, 46, 8342-8356
10. Piguet, C.; Borkovec, M.; Hamacek, J.; Zeckert, K. Coord. Chem. Rev. 2005, 249, 705-726
11. Natale, D.; Mareque-Rivas, J. C. Chem. Commun. 2008, 425-437
12. Sokolov, A. N.; Friscic, T.; MacGillivray, L. R. J. Am. Chem. Soc. 2006, 128, 2806-2807
13. Davois, A. M.; Teague, S. J. Angew. Chem., Int. Ed. Engl. 1999, 38, 736-749
14. Zordan, F.; Purver, S. L.; Adams, H.; Brammer, L. CrystEngComm 2005, 7, 350-354
15. Chulkova, T. G.; Gushchin, P. V.; Haukka, M.; Kukushkin, V. Y. Inorg. Chem. Commun. 2010, 13, 580-583
16. Au, R. H. W.; Fraser, C. S. A.; Eisher, D. J.; Jenninngs, M. C.; Puddephatt, R. J. Organometallics 2009, 28, 1719-1729
17. Chakraborty, J.; Figge, H. M.; Sheldrick, W. S.; Banerjee, P. Polihedron 2005, 24, 771-776
18. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem., Int. Ed. Engl. 2008, 47, 6114-6121
19. Formiguè, M.; Batail, P. Chem. Rev. 2004, 104, 5379-5418
20. Crihfield, A.; Hartwell, J.; Phelps, D.; Walsh, R. B.; Harris, J. L.; Payne, J. F.; Pennington, W. T.; Hanks, T. W. Cryst. Growth Des. 2003, 3, 313-320
21. Legon, A. C. Angew. Chem., Int. Ed. Engl. 1999, 38, 2686-2714
22. Roper, L. C.; Prasang, C.; Kozhevnikov, V. N.; Whitwood, A. C.; Karadakov, P. B.; Bruce, D. W. Cryst. Growth Des. 2010, 10, 3710-3720
23. Kilpin, K. J.; Gower, M. L.; Telfer, S. G.; Jameson, G. B.; Crowley, J. D. Inorg. Chem. 2011, 50, 1123-1134
24. Moussa, J.; Amouri, H. Angew. Chem., Int. Ed. Engl. 2008, 47, 1372-1380
25. Moussa, J.; Wong, K. M. C.; Chamoreau, M. L.; Amouri, H.; Yam, V. W. W. Dalton Trans. 2007, 3526-3530
26. Delahaye, S.; Loosli, C.; Liu, S. X.; Decurtins, S.; Labat, G.; Neels, A.; Loosli, A.; Ward, T. R.; Hauser, A. Adv. Funct. Mater. 2006, 16, 286-295
27. Shan, X. F.; Wang, D. H.; Tung, C. H.; Wu, L. Z. Tetrahedron 2008, 64, 5577-5582
28. Ueda, K.; Sugimoto, T.; Faulmann, C.; Cassoux, P. Eur. J. Inorg. Chem. 2003, 2333-2338
29. Smucker, B. W.; Hudson, J. M.; Omary., M. A.; Dunbar, K. R. Inorg. Chem. 2003, 42, 4714-4723
30. Fischer, R. A.; Woll, C. Angew. Chem., Int. Ed. Engl. 2009, 48, 2-6
31. Friese, V. A.; Kurth, D. G. Coord. Chem. Rev. 2008, 252, 199-211
32. Holliday, B. J.; Mirkin, C. A. Angew. Chem., Int. Ed. Engl. 2001, 40, 2022-2043
33. Schneider, H. J. Angew. Chem., Int. Ed. Engl. 2009, 48, 3924-3977
34. Notrhrop, B. H.; Zheng, Y. R.; Chi, K. W.; Stang, P. J. Acc. Chem. Res. 2009, 42, 1554-1563
35. Han, Z.; Zhao, Y.; Peng, J.; Tian, A.; Liu, Q.; Ma, J.; Wang, E.; Hu, N. CrystEngComm 2005, 7, 380-387
36. Kimizuka, N. Adv. Mater. 2000, 12, 1461-1463
37. Katz, H. E.; Hong, X. M.; Dodabalapur, A.; Sarpeshkar, R. J. Appl. Phys. 2002, 91, 1572-1567
38. Drury, C. J.; Mutsaers, C. M. J.; Hart, C. M.; Matters, M.; de Leeuw, D. M. Appl. Phys. Lett. 1998, 73, 108-110
39. Halik, M.; Klauk, H.; Zschieschang, U.; Kriem, T.; Schmid, G.; Radlik, W.; Wussow, K. Appl. Phys. Lett. 2002, 81, 289-291
40. Halik, M.; Klauk, H.; Zschieschang, U.; Schmid, G.; Radlik, W.; Ponomarenko, S.; Kirchmeyer, S.; Weber, W. J. Appl. Phys. 2003, 93, 2977-2981
41. Gelinck, G. H.; Geuns, T. C. T.; de Leeuw, D. M. Appl. Phys. Lett. 2000, 77, 1487-1489
42. Sirringhaus, H.; Tessler, N.; Friend, R. H. Science 1998, 280, 1741-1744
43. Haukka, S.; Root, A. J. Phys. Chem. 1994, 98, 1695-1703
44. Maier, G. Prog. Polym. Sci. 2001, 26, 3-65
45. Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99-117
46. Guillaud, G.; Simon, J.; Germain, J. P. Coord. Chem. Rev. 1998, 178-180, 1433-1484
47. Lavina, S.; Negro, E.; Pace, G.; Gross, S.; Depaoli, G.; Vidali, M.; Di Noto, V. J. Non-Cryst. Solids 2007, 353, 2878-2888
48. Gross, S.; Di Noto, V.; Schubert, U. J. Non-Cryst. Solids 2003, 322, 154-159
49. Di Noto, V; Boeer, A. B.; Lavina, S.; Muryn, C. A.; Bauer, M.; Timco, G. A.; Negro, E.; Rancan, M.; Winpenny, R. E. P.; Gross, S. Adv. Funct. Mater. 2009, 19, 1-11
50. Lu, W.; Chen, Y.; Roy, V. A. L.; Chui, S. S. Y.; Che, C. M. Angew. Chem., Int. Ed. Engl. 2009, 48, 7621-7625
51. Jiung, H.; Lin, W. J. Organomet. Chem. 2005, 690, 5159-5169
52. Frischmann, P. D.; Guieu, S.; Tabeshi, R.; MacLachlan, M. J. J. Am. Chem. Soc. 2010, 132, 7668-7675
53. Bassetti, M. Eur. J. Inorg. Chem. 2006, 4473-4482
54. Kuroiwa, K.; Oda, N.; Kimizuka, N. Sci. Tech. Adv. Mater. 2006, 7, 629-634
55. Gerhardt, W. W.; Zucchero, A. J.; South, C. R.; Bunz, U. H. F.; Weck, M. Chem.-Eur. J. 2007, 13, 4467-4474
56. Au, R. H. W.; Jennings, M. C.; Puddephatt, R. J. Eur. J. Inorg. Chem. 2009, 1526-1534
57. Shamnugaraju, S.; Bar, A. K.; Chi, K. W.; Mucherjen, P. S. Organometallics 2010, 29, 2971-2980
58. Machut, C.; Patrigeon, J.; Tilloy, S.; Briciut, H.; Hapiot, F.; Monflier, E. Angew. Chem., Int. Ed. Engl. 2007, 46, 3040-3042
59. Haxwell, S. M.; Espallargas, G. M.; Bradshaw, D.; Rosseinsky, M. J.; Prior, T. J.; Florence, A. J.; van de Streek, J.; Brammer, L. Chem. Commun. 2007, 1532-1534
60. Kitagawa, S.; Kitaura, R.; Noro, S. Angew. Chem., Int. Ed. Engl. 2004, 43, 2334-2375
61. Bureekae, W. S.; Shomirura, S.; Kitakawa, S. Sci. Technol. Adv. Mater. 2008, 9, 1-12
62. Lu, W.; Chen, Y.; Roy, V. A. L.; Chiu, S. S. Y.; Che, C. Angew. Chem., Int. Ed. Engl. 2009, 48, 7621-7625
63. Jiang, H.; Lin, W. J. Organomet. Chem. 2005, 690, 5159-5169
64. Cooke, M. W.; Chartrand, D.; Hanan, G. S. Coord. Chem. Rev. 2008, 252, 903-921
65. Umakoshi, K.; Kojima, T.; Saito, K.; Akatsu, S.; Onischi, M.; Ishizaka, S.; Kitamura, N.; Nakao, Y.; Sakaki, S.; Ozawa, Y. Inorg. Chem. 2008, 47, 5033-5035
66. Ziessel, R.; Hissler, M.; El-ghayoury, A.; Harriman, A. Coord. Chem. Rev. 1998, 178-180, 1251-1298
67. Kuroiwa, K.; Shibata, T.; Sasaki, S.; Ohba, M.; Takahara, A.; Kunitake, T.; Kimizuka, N. J. Pol. Sci.: Part A: Polym. Chem. 2006, 44, 5192-5202
68. Shirahata, T.; Kibune, M.; Mausato, M.; Kawashima, T.; Saito, G.; Imakubo, T. J. Mater. Chem. 2006, 16, 3381-3390
69. Cavallo, G.; Metrangolo, P.; Pilati, T.; Resnati, G.; Sansotera, M.; Terraneo, G. Chem Soc. Rev. 2010, 39, 3772-3783
70. Yamamoto, H. M. Riken Rev. 2002, 46, 3-6
71. Huang, X. Q.; Zhang, H. H.; Guo, C. Y.; Zhou, Z. Y.; Zheng, N. F. Angew. Chem., Int. Ed. Engl. 2009, 48, 1-6
72. Jude, H.; Sinclair, D. J.; Das, N.; Sherburn, M. S.; Stang, P. J. J. Org. Chem.. 2006, 71, 4155-4163
73. Ghosh, S.; Batten, S. R.; Turner, D. R.; Mukherjee, P. S. Organometallics 2007, 26, 3252-3255
74. Saba, B. K.; Nangia, A. Cryst. Growth Des. 2007, 7, 393-401
75. Lu, W.; Naj, K. M.; Che, C. M. Chem. Asian J. 2009, 4, 830-834
76. Kimizuka, N.; Oda, N.; Kunitake, T. Inorg. Chem. 2000, 39, 2684-2689
77. Bremi, J.; Fontana, M.; Caseri, W.; Smith, P. Macromol. Symp. 2006, 235, 80-88
78. Fontana, M.; Chanzy, H.; Caseri, W. R.; Smith, P.; Schenning, A. P. H. J.; Meijer, E. W.; Gröhn, F. Chem. Mater. 2002, 14, 1730-1735
79. Femoni, C.; Iapalucci, M. C.; Longoni, G.; Lovato, T.; Stagni, S.; Zacchini, S. Inorg. Chem. 2010, 49, 5992-6004
80. Belluco, U.; Bertani, R.; Michelin, R. A.; Mozzon, M. J. Organomet. Chem. 2000, 600, 37-55
81. Cardolaccia, F.; Li, Y.; Shanzu, K. S. J. Am. Chem. Soc. 2008, 130, 2535-2545
82. Xu, R.; Schweizer, W. B.; Frauenrath, H. J. Am. Chem. Soc. 2008, 130, 11437-11445
83. Wong, W. Y.; Ho, C. L. Coord. Chem. Rev. 2006, 250, 2627-2690
84. Tam, A. Y. Y.; Wong, K. M. C.; Yam, V. W. W. Chem.-Eur. J. 2009, 15, 4775-4778
85. Saha, B. K.; Nangia, A. Cryst. Growth Des. 2007, 7, 393-401
86. La Groia, A.; Ricci, A.; Bassetti, M.; Masi, D.; Bianchini, C.; Lo Sterzo, C. J. Organomet. Chem. 2003, 683, 406-420
87. Shiotsuka, M.; Nishito, N.; Keyaki, K.; Nozaki, K. Dalton Trans. 2010, 29, 1831-1835
88. Chen, Y.; Li, K.; Lu, W.; Chui, S. S. Y.; Ma, C. W.; Che, C. M. Angew. Chem., Int. Ed. Engl. 2009, 48, 9909-9913
89. Bertani, R.; Sgarbossa, P.; Venzo, A.; Lely, F.; Amati, M.; Resnati, G.; Pilati, T.; Metrangolo, P.; Terraneo, G. Coord. Chem. Rev. 2010, 254, 677-695
90. Brammer, L.; Espallargas, G. M.; Libri, S. CrystEngComm 2008, 10, 1712-1727
91. Mareque-Rivas, J. C.; Brammer, L. Coord. Chem. Rev. 1999, 183, 43-80
92. Adams, C. J.; Bowen, L. E. Dalton Trans. 2005, 2239-2240
93. Yoshida, T.; Otsuka, S.; Jones, D. G.; Spencer, J. L.; Binger, P.; Brinkmann, A.; Wedemann, P. Inorg. Synth. 1990, 28, 113-114
94. Baldrighi, M.; Metrangolo, P.; Meyer, F.; Pilati, T.; Proserpio, D.; Resnati, G.; Terraneo, G. J. Fluorine Chem. 2010, 131, 1218-1224
95. Di Noto, V. J. Phys. Chem. B 2002, 106, 11139-11154
96. Burla, M. C.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; Giacovazzo, C.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 2003, 36, 1103-1112
97. Sheldrick, G. M. Acta Crystallogr. A 2008, 64, 112-122
98. Adachi, K. In Dielectric Spectroscopy of Polymeric Materials. Fundamentals and Applications; Runt, J. P.; Fitzgerald, J. J., Eds.; American Chemical Society: Washington, DC, 1997; pp 261-282.
99. Mead, D. J.; Fuoss, R. M. J. Am. Chem. Soc. 1942, 64, 2389-2393
100. Ku, C. C.; Liepins, R. In Electrical Properties of Polymers: Chemical Principles; Hanser: Munich, 1987.
101. Semiconductor Industry Association. International Technology Roadmap for Semiconductors (ITRS), (2005) Update (http://www.itrs.net/links/2005ITRS/ interconnect2005.pdf).