Enhanced solubilization of large-diameter single-walled carbon nanotubes with amino-functionalized dipyrene nanotweezers
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Pyrene-based nanotweezers 1 consisting of two pyrenes and amino-substituted carbazole in between have been successfully synthesized via Suzuki–Miyaura coupling reaction. The supramolecular complex formation of nanotweezers 1 with single-walled carbon nanotubes (SWNTs) was studied, and it was found that nanotweezers 1 exhibited much higher the SWNTs extraction ability as compared to the analogous dipyrene nanotweezers 2 and 3 with soluble alkyl-substituents. This enhanced extraction ability of 1 can be attributed to the formation of more stable SWNT complexes in methanol. On the basis of photoluminescence excitation and UV–Vis-NIR absorption of 76-CoMoCAT SWNTs before and after the extraction, nanotweezers 1 were found to show high selectivity towards (8,4)-, (7,6)-, (9,4)-, and (8,6)-SWNTs with diameter ranging from 0.84 to 0.97 nm.
KeywordsRadial Breathing Mode Extraction Ability Typical Atomic Force Microscopy Image Miyaura Coupling Reaction Pyrene Moiety
Dr. Feng Wang wishes to thank Prof. Naoki Komatsu at Shiga University of Medical Science for the long-time support and encouragement. This work was financially supported by Natural Science Foundation of China (Grant No. 51103111), Education Ministry of China (Program for NCET-12-0714), the Scientific Research Foundation for the Returned Overseas Chinese Scholars, the Open Fund of the State Key Laboratory of Luminescent Materials and Devices (2014-skllmd-11), and Graduate Innovative Fund of Wuhan Institute of Technology (Grant No. CX2013009).
- 28.Wang F, Matsuda K, Rahman AM, Peng X, Kimura T, Komatsu N (2010) Simultaneous discrimination of handedness and diameter of single-walled carbon nanotubes (swnts) with chiral diporphyrin nanotweezers leading to enrichment of a single enantiomer of (6, 5)-swnts. J Am Chem Soc 132:10876–10881CrossRefGoogle Scholar
- 35.Li Y, Wang X, Lv R, Wang F (2014) Non-covalent separation of optically active single-walled carbon nanotubes. Prog Chem 26:1361–1368Google Scholar
- 38.Backes C, Schmidt CD, Hauke F, Hirsch A (2011) Perylene-based nanotweezers: enrichment of larger-diameter single-walled carbon nanotubes. Chem Eur J 6:438–444Google Scholar
- 46.Maeda Y, Kimura S, Kanda M, Hirashima Y, Hasegawa T, Wakahara T, Lian Y, Nakahodo T, Tsuchiya T, Akasaka T, Lu J, Zhang X, Gao Z, Yu Y, Nagase S, Kazaoui S, Minami N, Shimizu T, Tokumoto H, Saito R (2005) Large-scale separation of metallic and semiconducting single-walled carbon nanotubes. J Am Chem Soc 127:10287–10290CrossRefGoogle Scholar