Separation of left- and right-handed semiconducting single-walled carbon nanotube enantiomers using achiral amino acid surfactant

References

• Green, A. A.; Duch, M. C.; Hersam, M. C. Isolation of Single-Walled Carbon Nanotube Enantiomers by Density Differentiation. Nano Res. 2009, 2, 69–77. DOI: 10.1007/s12274-009-9006-y.
   Web of Science ®Google Scholar
• Wang, F.; Matsuda, K.; Mustafizur Rahman, A. F. M.; Peng, X.; Kimura, T.; Komatsu, N. 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. 2010, 132, 10876–10881. DOI: 10.1021/ja1044677.
   PubMed Web of Science ®Google Scholar
• Qin, X.; Peng, F.; Yang, F.; He, X.; Huang, H.; Luo, D.; Yang, J.; Wang, S.; Liu, H.; Peng, L.; Li, Y. Growth of Semiconducting Single-Walled Carbon Nanotubes by Using Ceria as Catalyst Supports. Nano Lett. 2014, 14, 512–517. DOI: 10.1021/nl403515c.
   PubMed Web of Science ®Google Scholar
• Li, J.; Ke, C. T.; Liu, K.; Li, P.; Liang, S.; Finkelstein, G.; Wang, F.; Liu, J. Importance of Diameter Control on Selective Synthesis of Semiconducting Single-Walled Carbon Nanotubes. ACS Nano 2014, 8, 8564–8572. DOI: 10.1021/nn503265g.
   PubMed Web of Science ®Google Scholar
• Yang, F.; Wang, X.; Zhang, D.; Yang, J.; Luo, D.; Xu, Z.; Wei, J.; Wang, J. Q.; Xu, Z.; Peng, F.; et al. Chirality-Specific Growth of Single-Walled Carbon Nanotubes on Solid Alloy Catalysts. Nature 2014, 510, 522–524. DOI: 10.1038/nature13434.
   PubMed Web of Science ®Google Scholar
• Zhang, S.; Kang, L.; Wang, X.; Tong, L.; Yang, L.; Wang, Z.; Qi, K.; Deng, S.; Li, Q.; Bai, X.; et al. Arrays of Horizontal Carbon Nanotubes of Controlled Chirality Grown Using Designed Catalysts. Nature 2017, 543, 234–238. DOI: 10.1038/nature21051.
   PubMed Web of Science ®Google Scholar
• Pochorovski, I.; Wang, H.; Feldblyum, J. I.; Zhang, X.; Antaris, A. L.; Bao, Z. H-Bonded Supramolecular Polymer for the Selective Dispersion and Subsequent Release of Large-Diameter Semiconducting Single-Walled Carbon Nanotubes. J. Am. Chem. Soc. 2015, 137, 4328–4331. DOI: 10.1021/jacs.5b01704.
   PubMed Web of Science ®Google Scholar
• Lei, T.; Chen, X.; Pitner, G.; Philip Wong, H. S.; Bao, Z. Removable and Recyclable Conjugated Polymers for Highly Selective and High-Yield Dispersion and Release of Low-Cost Carbon Nanotubes. J. Am. Chem. Soc. 2016, 138, 802–805. DOI: 10.1021/jacs.5b12797.
   PubMed Web of Science ®Google Scholar
• Nish, A.; Hwang, J. Y.; Doig, JAND.; Nicholas, R. J. Highly Selective Dispersion of Single-Walled Carbon Nanotubes Using Aromatic Polymers. Nat. Nanotechnol. 2007, 2, 640–646. DOI: 10.1038/nnano.2007.290.
   PubMed Web of Science ®Google Scholar
• Zheng, M.; Jagota, A.; Strano, M. S.; Santos, A. P.; Barone, P. S.; Chou, G.; Diner, B. A.; Dresselhaus, M. S.; Mclean, R. S.; Onoa, G. B.; et al. Structure-Based Carbon Nanotube Sorting by Sequence-Dependent DNA Assembly. Science 2003, 302, 1545–1548. DOI: 10.1126/science.1091911.
   PubMed Web of Science ®Google Scholar
• Zheng, M.; Semke, E. D. Enrichment of Single Chirality Carbon Nanotubes. J. Am. Chem. Soc. 2007, 129, 6084–6085. DOI: 10.1021/ja071577k.
   PubMed Web of Science ®Google Scholar
• Zhang, M.; Khripin, C. Y.; Fagan, J. A.; McPhie, P.; Ito, Y.; Zheng, M. Single-Step Total Fractionation of Single-Wall Carbon Nanotubes by Countercurrent Chromatography. Anal. Chem. 2014, 86, 3980–3984. DOI: 10.1021/ac5003189.
   PubMed Web of Science ®Google Scholar
• (a) Liu, H.; Nishide, D.; Tanaka, T.; Kataura, H. Large-Scale Single-Chirality Separation of Single-Wall Carbon Nanotubes by Simple Gel Chromatography. Nat. Commun. 2011, 2, 309. (b) Liu, H.; Tanaka, T.; Kataura, H. Optical Isomer Separation of Single-Chirality Carbon Nanotubes Using Gel Column Chromatography. Nano Lett. 2014, 14, 6237–6243. DOI: 10.1021/nl5025613.
   Web of Science ®Google Scholar
• Krupke, R.; Hennrich, F.; Löhneysen, H. V.; Kappes, M. M. Separation of Metallic from Semiconducting Single-Walled Carbon Nanotubes. Science 2003, 301, 344–347. DOI: 10.1126/science.1086534.
   PubMed Web of Science ®Google Scholar
• Arnold, M. S.; Green, A. A.; Hulvat, J. F.; Stupp, S. I.; Hersam, M. C. Sorting Carbon Nanotubes by Electronic Structure Using Density Differentiation. Nat. Nanotechnol. 2006, 1, 60–65. DOI: 10.1038/nnano.2006.52.
   PubMed Web of Science ®Google Scholar
• Ghosh, S.; Bachilo, S. M.; Weisman, R. B. Advanced Sorting of Single-Walled Carbon Nanotubes by Nonlinear Density-Gradient Ultracentrifugation. Nat. Nanotechnol. 2010, 5, 443–450. DOI: 10.1038/nnano.2010.68.
   PubMed Web of Science ®Google Scholar
• Peng, X. B.; Komatsu, N.; Bhattacharya, S.; Shimawaki, T.; Aonuma, S.; Kimura, T.; Osuka, A. Optically Active Single-Walled Carbon Nanotubes. Nat. Nanotechnol. 2007, 2, 361–365. DOI: 10.1038/nnano.2007.142.
   PubMed Web of Science ®Google Scholar
• Peng, X. B.; Komatsu, N.; Kimura, T.; Osuka, A. Improved Optical Enrichment of SWNTs through Extraction with Chiral Nanotweezers of 2,6-Pyridylene-Bridged Diporphyrins. J. Am. Chem. Soc. 2007, 129, 15947–15953. DOI: 10.1021/ja075094s.
   PubMed Web of Science ®Google Scholar
• Peng, X. B.; Komatsu, N.; Kimura, T.; Osuka, A. Simultaneous Enrichments of Optical Purity and (n,m) Abundance of SWNTs through Extraction with 3,6-Carbazolylene-Bridged Chiral Diporphyrin Nanotweezers. ACS Nano 2008, 2, 2045–2050. DOI: 10.1021/nn800462s.
   PubMed Web of Science ®Google Scholar
• Akazaki, K.; Toshimitsu, F.; Ozawa, H.; Fujigaya, T.; Nakashima, N. Recognition and One-Pot Extraction of Right- and Left-Handed Semiconducting Single-Walled Carbon Nanotube Enantiomers Using Fluorene-Binaphthol Chiral Copolymers. J. Am. Chem. Soc. 2012, 134, 12700–12707. DOI: 10.1021/ja304244g.
   PubMed Web of Science ®Google Scholar
• Green, A. A.; Hersam, M. C. Nearly Single-Chirality Single-Walled Carbon Nanotubes Produced via Orthogonal Iterative Density Gradient Ultracentrifugation. Adv. Mater. 2011, 23, 2185–2190. DOI: 10.1002/adma.201100034.
   PubMed Web of Science ®Google Scholar
• Wei, X.; Tanaka, T.; Yomogida, Y.; Sato, N.; Saito, R.; Kataura, H. Experimental Determination of Excitonic Band Structures of Single-Walled Carbon Nanotubes Using Circular Dichroism Spectra. Nat. Commun. 2016, 7, 12899. DOI: 10.1038/ncomms12899.
   PubMed Web of Science ®Google Scholar
• Ao, G.; Streit, J. K.; Fagan, J. A.; Zheng, M. Differentiating Left- and Right-Handed Carbon Nanotubes by DNA. J. Am. Chem. Soc. 2016, 138, 16677–16685. DOI: 10.1021/jacs.6b09135.
   PubMed Web of Science ®Google Scholar
• Weisman, R. B.; Bachilo, S. M. Dependence of Optical Transition Energies on Structure for Single-Walled Carbon Nanotubes in Aqueous Suspension: An Empirical Kataura Plot. Nano Lett. 2003, 3, 1235–1238. DOI: 10.1021/nl034428i.
   Web of Science ®Google Scholar
• Bachilo, S. M.; Strano, M. S.; Kittrell, C.; Hauge, R. H.; Smalley, R. E.; Weisman, R. B. Structure-Assigned Optical Spectra of Single-Walled Carbon Nanotubes. Science 2002, 298, 2361–2366. DOI: 10.1126/science.1078727.
   PubMed Web of Science ®Google Scholar
• Kataura, H.; Kumazawa, Y.; Maniwa, Y.; Ohtsuka, Y.; Sen, R.; Suzuki, S.; Achiba, Y. Diameter Control of Single-Walled Carbon Nanotubes. Carbon 2000, 38, 1691–1697. DOI: 10.1016/S0008-6223(00)00090-7.
   Web of Science ®Google Scholar
• Toshimitsu, F.; Nakashima, N. Semiconducting Single-Walled Carbon Nanotubes Sorting with a Removable Solubilizer Based on Dynamic Supramolecular Coordination Chemistry. Nat. Commun. 2014, 5, 5041. DOI: 10.1038/ncomms6041.
   PubMed Web of Science ®Google Scholar
• Dukovic, G.; Balaz, M.; Doak, P.; Berova, N. D.; Zheng, M.; Mclean, R. S.; Brus, L. E. Racemic Single-Walled Carbon Nanotubes Exhibit Circular Dichroism When Wrapped with DNA. J. Am. Chem. Soc. 2006, 128, 9004–9005. DOI: 10.1021/ja062095w.
   PubMed Web of Science ®Google Scholar
• Naumov, A. V.; Ghosh, S.; Tsyboulski, D. A.; Bachilo, S. M.; Weisman, R. B. Analyzing Absorption Backgrounds in Single-Walled Carbon Nanotube Spectra. ACS Nano 2011, 5, 1639–1648. DOI: 10.1021/nn1035922.
   PubMed Web of Science ®Google Scholar
• Ghosh, S.; Bachilo, S. M.; Weisman, R. B. Removing Aggregates from Single-Walled Carbon Nanotube Samples by Magnetic Purification. J. Phys. Chem. C 2014, 118, 4489–4494. DOI: 10.1021/jp411941k.
   Web of Science ®Google Scholar