Electronic and electrochemical properties as well as flowerlike supramolecular assemblies of fulleropyrrolidines bearing ester substituents with different alkyl chain lengths

RSC Advances

Volumn 4, Issue 104, 2014, Pages 60342-60348

  Zhang, Xuan ^a   Li, Xu Dong ^a   Ma, Li Xia ^a   Zhang, Bei ^a  

^a DONGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTRA; BUTYRIC ACID; CYCLIC VOLTAMMETRY; DESIGN FOR TESTABILITY; ELECTROCHEMICAL PROPERTIES; ELECTRONIC STRUCTURE; ESTERIFICATION; ESTERS; FULLERENES; ORGANIC SOLVENTS; SCANNING ELECTRON MICROSCOPY; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY; X RAY DIFFRACTION;

ALKYL CHAIN LENGTHS; ELECTRONIC STRUCTURE CALCULATIONS; FLOWERLIKE ARCHITECTURES; FULLERENE DERIVATIVE; FULLEROPYRROLIDINE DERIVATIVES; REDUCTION POTENTIAL; SUPRAMOLECULAR ARCHITECTURES; SUPRAMOLECULAR ASSEMBLIES;

DENSITY FUNCTIONAL THEORY;

EID: 84912017608     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c4ra10654g     Document Type: Article

References (58)

1. C. Yang, J. Y. Kim, S. Cho, J. K. Lee, A. J. Heeger and F. Wudl, J. Am. Chem. Soc., 2008, 130, 6444-6450.
2. J. L. Segura, N. Martín and D. M. Guldi, Chem. Soc. Rev., 2005, 34, 31-47.
3. D. M. Guldi, B. M. Illescas, C. M. Atienza, M. Wielopolskia and N. Martín, Chem. Soc. Rev., 2009, 38, 1587-1597.
4. C.-Z. Li, H. L. Yip and A. K. Y. Jen, J. Mater. Chem., 2012, 22, 4161-4177.
5. Y. J. He and Y. F. Li, Phys. Chem. Chem. Phys., 2011, 13, 1970-1983.
6. Y.-Y. Lai, Y.-J. Cheng and C. S. Hsu, Energy Environ. Sci., 2014, 7, 1866-1883.
7. M. J. Hollamby, M. Karny, P. H. H. Bomans, N. A. J. M. Sommerdjik, A. Saeki, S. Seki, H. Minamikawa, I. Grillo, B. R. Pauw, P. Brown, J. Eastoe, H. Möhwald and T. Nakanishi, Nat. Chem., 2014, 6, 690-696.
8. H.-G. Li, J. Choi and T. Nakanishi, Langmuir, 2013, 29, 5394-5406.
9. Y. Yamamoto, G. Zhang, W. Jin, T. Fukushima, N. Ishii, A. Saeki, S. Seki, S. Tagawa, T. Minari, K. Tsukagoshi and T. Aida, Proc. Natl. Acad. Sci. U. S. A., 2009, 106, 21051-21056.
10. V. Georgakilas, F. Pellarini, M. Prato, D. M. Guldi, M. Melle-Franco and F. Zerbetto, Proc. Natl. Acad. Sci. U. S. A., 2002, 99, 5075-5080.
11. L. Sánchez, R. Otero, J. María Gallego, R. Miranda and N. Martín, Chem. Rev., 2009, 109, 2081-2091.
12. T. Nakanishi, Chem. Commun., 2010, 46, 3425-3436.
13. H.-G. Li, S. S. Babu, S. T. Turner, D. Neher, M. J. Hollamby, T. Seki, S. Yagai, Y. Deguchi, H. Möhwald and T. Nakanishi, J. Mater. Chem. C, 2013, 1, 1943-1951.
14. H. Asanuma, H.-G. Li, T. Nakanishi and H. Möhwald, Chem.-Eur. J., 2010, 16, 9330-9338.
15. P. Heremans, D. Cheyns and B. P. Rand, Acc. Chem. Res., 2009, 42, 1740-1747.
16. A. J. Moulé and K. Meerholz, Adv. Funct. Mater., 2009, 19, 3028-3036.
17. L. K. Shrestha, Q. M. Ji, T. Mori, K. Miyazawa, Y. Yamauchi, J. P. Hill and K. Ariga, Chem.-Asian J, 2013, 8, 1662-1679.
18. S. S. Babu, H. Möhwald and T. Nakanishi, Chem. Soc. Rev., 2010, 39, 4021-4035.
19. Y.-F. Shen and T. Nakanishi, Phys. Chem. Chem. Phys., 2014, 16, 7199-7204.
20. X. Zhang and M. Takeuchi, Angew. Chem., Int. Ed., 2009, 48, 9646-9651.
21. L. Wang, B. Liu, D. Liu, M. Yao, Y. Hou, S. Yu, T. Cui, D. Li, G. Zou, A. Iwasiewicz and B. Sundqvist, Adv. Mater., 2006, 18, 1883-1886.
22. J. Geng, W. Zhou, P. Skelton, W. Yue, I. A. Kinloch, A. H. Windle and B. F. G. Johnson, J. Am. Chem. Soc., 2008, 130, 2527-2534.
23. X. Zhang and X. D. Li, Chin. Chem. Lett., 2014, 25, 912-914.
24. L. Wei, J. Yao and H. Fu, ACS Nano, 2013, 7, 7573-7582.
25. K. Miyazawa, Y. Kuwasaki, A. Obayashi and M. Kuwabara, J. Mater. Res., 2002, 17, 83-88.
26. M. H. Nurmawati, P. K. Ajikumar, R. Renu, C. H. Sow and S. Valiyaveettil, ACS Nano, 2008, 2, 1429-1436.
27. M. Sathish, K. Miyazawa, J. P. Hill and K. Ariga, J. Am. Chem. Soc., 2009, 131, 6372-6373.
28. C. Park, H. J. Song and H. C. Choi, Chem. Commun., 2009, 4803-4805.
29. D. Mi, H.-U. Kim, J.-H. Kim, F. Xu, S.-H. Jin and D. H. Hwang, Synth. Met., 2012, 162, 483-489.
30. H. Yu, H.-H. Cho, C.-H. Cho, K.-H. Kim, D. Y. Kim, B. J. Kim and J. H. Oh, ACS Appl. Mater. Interfaces, 2013, 5, 4865-4871.
31. Y. J. He, H.-Y. Chen, J. H. Hou and Y. F. Li, J. Am. Chem. Soc., 2010, 132, 1377-1382.
32. C.-Z. Li, S.-C. Chien, H.-L. Yip, C.-C. Chueh, F.-C. Chen, Y. Matsuo, E. Nakamura and A. K. Y. Jen, Chem. Commun., 2011, 47, 10082-10084.
33. K.-H. Kim, H. Kang, S. Y. Nam, J. Jung, P. S. Kim, C.-H. Cho, C. Lee, S. C. Yoon and B. J. Kim, Chem. Mater., 2011, 23, 5090-5095.
34. I. Riedel, E. von Hauff, J. Parisi, N. Martin, F. Giacalone and V. Dyakonov, Adv. Funct. Mater., 2005, 15, 1979-1987.
35. N. Nakashima, T. Ishii, M. Shirakusa, T. Nakanishi, H. Murakami and T. Sagara, Chem.-Eur. J., 2001, 7, 1766-1772.
36. A. M. Cassell, C. L. Asplund and J. M. Tour, Angew. Chem., Int. Ed., 1999, 38, 2403-2405.
37. J.-F. Nierengarten, New J. Chem., 2004, 28, 1177-1191.
38. X. Y. Meng, Q. Xu, W. Q. Zhang, Z. A. Tan, Y. F. Li, Z. X. Zhang, L. Jiang, C. Y. Shu and C. R. Wang, ACS Appl. Mater. Interfaces, 2012, 4, 5966-5973.
39. A. L. Rosa, K. Gillemot, E. Leary, C. Evangeli, M. T. González, S. Filippone, G. Rubio-Bollinger, N. Agraït, C. J. Lambert and N. Martín, J. Org. Chem., 2014, 79, 4871-4877.
40. X. Y. Meng, G. Y. Zhao, Q. Xu, Z. A. Tan, Z. X. Zhang, L. Jiang, C. Y. Shu, C. R. Wang and Y. F. Li, Adv. Funct. Mater., 2014, 24, 158-163.
41. T. Homma, K. Harano, H. Isobe and E. Nakamura, J. Am. Chem. Soc., 2011, 133, 6364-6370.
42. T. Nakanishi, W. Schmitt, T. Michinobu, D. G. Kurth and K. Ariga, Chem. Commun., 2005, 5982-5984.
43. T. Nakanishi, Y.-F. Shen, J.-B. Wang, H.-G. Li, P. Fernandes, K. Yoshida, S. Yagai, M. Takeuchi, K. Ariga, D. G. Kurth and H. Möhwald, J. Mater. Chem., 2010, 20, 1253-1260.
44. T. Nakanishi, K. Ariga, T. Michinobu, K. Yoshida, H. Takahashi, T. Teranishi, H. Möhwald and D. G. Kurth, Small, 2007, 3, 2019-2023.
45. X. Zhang, T. Nakanishi, T. Ogawa, A. Saeki, S. Seki, Y. F. Shen, Y. Yamauchi and M. Takeuchi, Chem. Commun., 2010, 46, 8752-8754.
46. X. Zhang, L. X. Ma and X. D. Li, Synth. Met., 2014, DOI: 10.1016/j.synthmet.2014.09.030.
47. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford CT, 2010.
48. M. Maggini, G. Scorrano and M. Prato, J. Am. Chem. Soc., 1993, 115, 9798-9799.
49. H. Wang, Y. J. He, Y. F. Li and H. M. Su, J. Phys. Chem. A, 2012, 116, 255-262.
50. T. Suzuki, Y. Maruyama, T. Akasaka, W. Ando, K. Kobayashi and S. Nagasel, J. Am. Chem. Soc., 1994, 116, 1359-1363.
51. M. Carano, T. D. Ros, M. Fanti, K. Kordatos, M. Marcaccio, F. Paolucci, M. Prato, S. Roffia and F. Zerbetto, J. Am. Chem. Soc., 2003, 125, 7139-7144.
52. C. J. Brabec, A. Cravino, D. Meissner, N. S. Sariciftci, T. Fromherz, M. T. Rispens, L. Sanchez and J. C. Hummelen, Adv. Funct. Mater., 2001, 11, 374-380.
53. M. C. Scharber, D. Mühlbacher, M. Koppe, P. Denk, C. Waldauf, A. J. Heeger and C. J. Brabec, Adv. Mater., 2006, 18, 789-794.
54. F. B. Kooistra, J. Knol, F. Kastenberg, L. M. Popescu, W. Verhees, J. H. Kroon and J. M. Hummelen, Org. Lett., 2007, 9, 551-554.
55. G. D. Han, W. R. Collins, T. L. Andrew, V. Bulović and T. M. Swager, Adv. Funct. Mater., 2013, 23, 3061-3069.
56. X. Zhang and X. D. Li, Chin. Chem. Lett., 2014, 25, 501-504.
57. The comparison of the HOMO and LUMO energies as well as energy gaps of C60 and PCBM calculated with various basis sets and experimental values were listed in Table S1 (ESI†). It showed that the PBEPBE/6-311G(d,p) basis set is more reliable than B3LYP/6-311G(d,p) for energy calculation based on geometry optimized with B3LYP/6-31G(d). Energies calculated from PBEPBE/6-311G(d,p) based on geometry optimized at the same level and at B3LYP/6-31G(d) level exhibited the comparable value but the former is more cost in computation time. Therefore, we selected the B3LYP/6-31G(d) level for geometry optimization but the PBEPBE/6-311G(d,p) for energy calculation by considering both reliability and computation cost.
58. S. S. Babu, A. Saeki, S. Seki, H. Möhwald and T. Nakanishi, Phys. Chem. Chem. Phys., 2011, 13, 4830-4834.