Selective dispersion of semiconducting single-walled carbon nanotubes with aromatic polyimides

References

• Iijima, S.; Ichihashi, T. Single-Shell Carbon Nanotubes of 1-nm Diameter. Nature 1993, 363, 603–605. DOI: 10.1038/363603a0.
   Web of Science ®Google Scholar
• Bethune, D. S.; Kiang, C. H.; de Vries, M. S.; Gorman, G.; Savoy, R.; Vazquez, J.; Beyers, R. Cobalt-Catalysed Growth of Carbon Nanotubes with Single-Atomic-Layer Walls. Nature 1993, 363, 605–607. DOI: 10.1038/363605a0.
   Web of Science ®Google Scholar
• Baughman, R. H.; Zakhidov, A. A.; Heer, W. A. Carbon Nanotubes-the Route towards Applications. Science 2002, 297, 787–792. DOI: 10.1126/science.1060928.
   PubMed Web of Science ®Google Scholar
• Ajayan, P. M. Nanotubes from Carbon. Chem Rev. 1999, 99, 1787–1800. DOI: 10.1021/cr970102g.
   PubMed Web of Science ®Google Scholar
• Chen, J.; Hamon, M. A.; Hu, H.; Chen, Y. S.; Rao, A. M.; Eklund, P. C.; Haddon, R. C. Solution Properties of Single-Walled Carbon Nanotubes. Science 1998, 282, 95–98. DOI: 10.1126/science.282.5386.95.
   PubMed Web of Science ®Google Scholar
• Wang, G.; Wei, X.; Tanaka, T.; Kataura, H. Diameter-Selective Separation of Semiconducting Single-Walled Carbon Nanotubes in Large Diameter Range. Phys. Status Solidi B. 2017, 254, 1700294–1700294. DOI: 10.1002/pssb.201700294.
   Google Scholar
• Moshammer, K.; Hennrich, F.; Kappes, M. M. Selective Suspension in Aqueous Sodium Dodecyl Sulfate according to Electronic Structure Type Allows Simple Separation of Metallic from Semiconducting Single-Walled Carbon Nanotubes. Nano Res. 2009, 2, 599–606. DOI: 10.1007/s12274-009-9057-0.
   Web of Science ®Google Scholar
• Subbaiyan, N. K.; Cambre, S.; Parra-Vasquez, A. N. G.; Haroz, E. H.; Doorn, S. K.; Duque, J. G. Role of Surfactants and Salt in Aqueous Two-Phase Separation of Carbon Nanotubes toward Simple Chirality Isolation. ACS Nano 2014, 8, 1619–1628. DOI: 10.1021/nn405934y.
   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
• Peng, X.; 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
• 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
• Lei, T.; Pochorovski, I.; Bao, Z. Separation of Semiconducting Carbon Nanotubes for Flexible and Stretchable Electronics Using Polymer Removable Method. Acc. Chem. Res. 2017, 50, 1096–1104. DOI: 10.1021/acs.accounts.7b00062.
   PubMed Web of Science ®Google Scholar
• Tulevski, G. S.; Franklin, A. D.; Frank, D.; Lobez, J. M.; Cao, Q.; Park, H.; Afzali, A.; Han, S.-J.; Hannon, J. B.; Haensch, W. Toward High-Performance Digital Logic Technology with Carbon Nanotubes. ACS Nano. 2014, 8, 8730–8745. DOI: 10.1021/nn503627h.
   PubMed Web of Science ®Google Scholar
• Chen, R. J.; Zhang, Y. G.; Wang, D. W.; Dai, H. J. Noncovalent Sidewall Functionalization of Single-Walled Carbon Nanotubes for Protein Immobilization. J. Am. Chem. Soc. 2001, 123, 3838–3839. DOI: 10.1021/ja010172b.
   PubMed Web of Science ®Google Scholar
• Feng, Y.; Miyata, Y.; Matsuishi, K.; Kataura, H. High-Efficiency Separation of Single-Wall Carbon Nanotubes by Self-Generated Density Gradient Ultracentrifugation. J. Phys. Chem. C. 2011, 115, 1752–1756. DOI: 10.1021/jp1100329.
   Web of Science ®Google Scholar
• Prantner, A. M.; Chen, J.; Murray, C. B.; Scholler, N. Coating Evaluation and Purification of Monodisperse, Water-Soluble, Magnetic Nanoparticles Using Sucrose Density Gradient Ultracentrifugation. Chem Mater. 2012, 24, 4008–4010. DOI: 10.1021/cm302582z.
   PubMed Web of Science ®Google Scholar
• Miller, R. D.; Michl, J. Polysilane High Polymers. Chem. Rev. 1989, 89, 1359–1410. DOI: 10.1021/cr00096a006.
   Web of Science ®Google Scholar
• Fukumaru, T.; Toshimitsu, F.; Fujigaya, T.; Nakashima, N. Effects of the Chemical Structure of Polyfluorene on Selective Extraction of Semiconducting Single-Walled Carbon Nanotubes. Nanoscale 2014, 6, 5879–5886. DOI: 10.1039/c4nr00809j.
   PubMed Web of Science ®Google Scholar
• Xu, W.; Zhao, J.; Qian, L.; Han, X.; Wu, L.; Wu, W.; Song, M.; Zhou, L.; Su, W.; Wang, C.; et al. Sorting of Large-Diameter Semiconducting Carbon Nanotube and Printed Flexible Driving Circuit for Organic Light Emitting Diode (OLED). Nanoscale 2014, 6, 1589–1595. DOI: 10.1039/c3nr04870e.
   PubMed Web of Science ®Google Scholar
• Ding, J.; Li, Z.; Lefebvre, J.; Cheng, F.; Dubey, G.; Zou, S.; Finnie, P.; Hrdina, A.; Scoles, L.; Lopinski, G. P.; et al. Enrichment of Large-Diameter Semiconducting SWCNTs by Polyfluorene Extraction for High Network Density Thin Film Transistors. Nanoscale 2014, 6, 2328–2339. DOI: 10.1039/c3nr05511f.
   PubMed Web of Science ®Google Scholar
• Chen, F.; Wang, B.; Chen, Y.; Li, L.-J. Toward the Extraction of Single Species of Single-Walled Carbon Nanotubes Using Fluorene-Based Polymers. Nano Lett. 2007, 7, 3013–3017. DOI: 10.1021/nl071349o.
   PubMed Web of Science ®Google Scholar
• Gomulya, W.; Costanzo, G. D.; de Carvalho, E. F.; Bisri, S. Z.; Derenskyi, V.; Fritsch, M.; Fröhlich, N.; Allard, S.; Gordiichuk, P.; Herrmann, A.; et al. Semiconducting Single-Walled Carbon Nanotubes on Demand by Polymer Wrapping. Adv. Mater. 2013, 25, 2948–2956. DOI: 10.1002/adma.201300267.
   PubMed Web of Science ®Google Scholar
• Tange, M.; Okazaki, T.; Iijima, S. Selective Extraction of Large-Diameter Single-Wall Carbon Nanotubes with Specific Chiral Indices by Poly(9,9-dioctylfluorene-alt-benzothiadiazole). J. Am. Chem. Soc. 2011, 133, 11908–11911. DOI: 10.1021/ja204698d.
   PubMed Web of Science ®Google Scholar
• Gao, J.; Kwak, M.; Wildeman, J.; Herrmann, A.; Loi, M. A. Effectiveness of Sorting Single-Walled Carbon Nanotubes by Diameter Using Polyfluorene Derivatives. Carbon 2011, 49, 333–338. DOI: 10.1016/j.carbon.2010.09.036.
   Web of Science ®Google Scholar
• Ozawa, H.; Ide, N.; Fujigaya, T.; Niidome, Y.; Nakashima, N. One-Pot Separation of Highly Enriched (6,5)-Single-Walled Carbon Nanotubes Using a Fluorene-Based Copolymer. Chem. Lett. 2011, 40, 239–241. DOI: 10.1246/cl.2011.239.
   Web of Science ®Google Scholar
• do Nascimento, G. M.; Silva, T. B.; Corio, P.; Dresselhaus, M. S. Charge-Transfer Behavior of Polyaniline Single Wall Carbon Nanotubes Nanocomposites Monitored by Resonance Raman Spectroscopy. J. Raman Spectrosc. 2010, 41, 1587–1593. DOI: 10.1002/jrs.2598.
   Web of Science ®Google Scholar
• Lee, H. W.; Yoon, Y.; Park, S.; Oh, J. H.; Hong, S.; Liyanage, L. S.; Wang, H.; Morishita, S.; Patil, N.; Park, Y. J.; et al. Selective Dispersion of High Purity Semiconducting Single-Walled Carbon Nanotubes with Regioregular Poly(3-alkylthiophene)s. Nat Commun. 2011, 2, 541. DOI: 10.1038/ncomms1545.
   PubMed Web of Science ®Google Scholar
• Wang, H.; Koleilat, G. I.; Liu, P.; Jimenez-Oses, G.; Lai, Y.-C.; Vosgueritchian, M.; Fang, Y.; Park, S.; Houk, K. N.; Bao, Z. High-Yield Sorting of Small-Diameter Carbon Nanotubes for Solar Cells and Transistors. ACS Nano 2014, 8, 7550–7550. DOI: 10.1021/nn503452b.
   PubMed Web of Science ®Google Scholar
• Von Bargen, C. D.; MacDermaid, C. M.; Lee, O.-S.; Deria, P.; Therien, M. J.; Saven, J. G. Origins of the Helical Wrapping of Phenyleneethynylene Polymers about Single-Walled Carbon Nanotubes. J. Phys. Chem. B. 2013, 117, 12953–12965. DOI: 10.1021/jp402140t.
   PubMed Web of Science ®Google Scholar
• Chung, W.; Nobusawa, K.; Kamikubo, H.; Kataoka, M.; Fujiki, M.; Naito, M. Time-Resolved Observation of Chiral-Index-Selective Wrapping on Single-Walled Carbon Nanotube with Non-Aromatic Polysilane. J. Am. Chem. Soc. 2013, 135, 2374–2383. DOI: 10.1021/ja311799m.
   PubMed Web of Science ®Google Scholar
• Naito, M.; Nobusawa, K.; Onouchi, H.; Nakamura, M.; Yasui, K-i.; Ikeda, A.; Fujiki, M. Stiffness- and Conformation-Dependent Polymer Wrapping onto Single-Walled Carbon Nanotubes. J. Am. Chem. Soc. 2008, 130, 16697–16703. DOI: 10.1021/ja806109z.
   PubMed Web of Science ®Google Scholar
• Gao, J.; Huang, Y.; Lian, Y. Selective Extraction of Metallic Arc-Discharged Single-Walled Carbon Nanotubes by a Water Soluble Polymethylsilane Derivative. RSC Adv. 2015, 5, 102238–102246. DOI: 10.1039/C5RA17761H.
   Web of Science ®Google Scholar
• Wang, H.; Li, B.; Mei, J.; Gao, C.; Li, Z.; Xu, S. Fabrication and Characterization of Novel Ag2O-Polyimide Composites with Enhanced Visible-Light Photocatalytic Activity. Fuller. Nanotub. Car. N. 2019, 27, 410–416. DOI: 10.1080/1536383X.2019.1578753.
   Web of Science ®Google Scholar
• Jiao, Q.; Zhang, S.; Wang, J.; Li, H.; Wu, Q.; Zhao, Y. In Situ Preparation of PI/Amino-Functionalized Graphene Composites and Their Properties. Fuller. Nanotub. Car. N. 2015, 23, 680–686. DOI: 10.1080/1536383X.2014.967848.
   Web of Science ®Google Scholar
• Takassi, M. A.; Zadehnazari, A. Nanocomposites of Triazole Functionalized Multi-Walled Carbon Nanotube with Chemically Grafted Polyimide: Preparation, Characterization, and Properties. Fuller. Nanotub. Car. N. 2016, 24, 128–238. DOI: 10.1080/1536383X.2015.1115976.
   Web of Science ®Google Scholar
• Fink, D.; Vacik, J.; Grünwald, R.; Klett, R.; Chadderton, L. T.; Hnatowicz, V. Modification of Polyimide by Energetic C60+ Ions. Fuller. Nanotub. Car. N. 1997, 5, 267–274. DOI: 10.1080/15363839708011987.
   Web of Science ®Google Scholar
• Wang, Y.; Shang, M.; Wang, Y.; Cui, B.; Qiu, Z.; Li, H.; Wang, Y. Polyimide Composite Films Reinforced by Graphene Quantum Dots. Fuller. Nanotub. Car. N. 2021, 2021, 1–9. DOI: 10.1080/1536383X.2021.2011237.
   Google Scholar
• Liu, C.; Liu, B.; Chan-Park, M. B. Synthesis of Polycaprolactone-Polyimide-Polycaprolactone Triblock Copolymers via a 2-Step Sequential Copolymerization and Their Application as Carbon Nanotube Dispersants. Polym. Chem. 2017, 8, 674–681. DOI: 10.1039/C6PY01933A.
   Web of Science ®Google Scholar
• Zhang, K.; Niu, H.; Wang, C.; Bai, X.; Lian, Y.; Wang, W. Novel Aromatic Polyimides with Pendent Triphenylamine Units: Synthesis, Photophysical, Electrochromic Properties. J. Electroanal. Chem. 2012, 682, 101–109. DOI: 10.1016/j.jelechem.2012.06.018.
   Web of Science ®Google Scholar
• Itkis, M. E.; Perea, D. E.; Niyogi, S.; Rickard, S. M.; Hamon, M. A.; Hu, H.; Zhao, B.; Haddon, R. C. Purity Evaluation of as-Prepared Single-Walled Carbon Nanotube Soot by Use of Solution-Phase near-IR Spectroscopy. Nano Lett. 2003, 3, 309–314. DOI: 10.1021/nl025926e.
   Web of Science ®Google Scholar
• Jorio, A.; Saito, R.; Hafner, J. H.; Lieber, C. M.; Hunter, M.; McClure, T.; Dresselhaus, G.; Dresselhaus, M. S. Structural (n, m) Determination of Isolated Single-Wall Carbon Nanotubes by Resonant Raman Scattering. Phys. Rev. Lett. 2001, 86, 1118–1121. DOI: 10.1103/PhysRevLett.86.1118.
   PubMed Web of Science ®Google Scholar
• Araujo, P. T.; Maciel, I. O.; Pesce, P. B. C.; Pimenta, M. A.; Doorn, S. K.; Qian, H.; Hartschuh, A.; Steiner, M.; Grigorian, L.; Hata, K.; Jorio, A. Nature of the Constant Factor in the Relation between Radial Breathing Mode Frequency and Tube Diameter for Single-Wall Carbon Nanotubes. Phys. Rev. B. 2008, 77, 241403. DOI: 10.1103/PhysRevB.77.241403.
   Web of Science ®Google Scholar
• Faulques, E.; Kalashnyk, N.; Slade, C. A.; Sanchez, A. M.; Sloan, J.; Ivanov, V. G. Vibrational and Electronic Structures of Tin Selenide Nanowires Confined inside Carbon Nanotubes. Synthetic Met. 2022, 284, 116968. DOI: 10.1016/j.synthmet.2021.116968.
   Google Scholar
• Deria, P.; Bargen, C.; Olivier, J. H.; Kumbhar, A. S.; Saven, J. G.; Therien, M. J. Single-Handed Helical Wrapping of Single-Walled Carbon Nanotubes by Chiral, Ionic, Semiconducting Polymers. J. Am. Chem. Soc. 2013, 135, 16220–16234. DOI: 10.1021/ja408430v.
   PubMed Web of Science ®Google Scholar
• Zhang, Y.; Wang, M.; Li, D.; Zhao, H.; Li, Y. Separation of Single-Walled Carbon Nanotubes Using the Amino Acid Surfactant N-Cocoyl Sarcosinate. ACS Appl. Nano Mater. 2019, 2, 5440–5449. DOI: 10.1021/acsanm.9b01054.
   Web of Science ®Google Scholar
• Kar, T.; Bettinger, H. F.; Scheiner, S.; Roy, A. K. Noncovalent pi-pi Stacking and CH Center Dot Center Dot Center Dot pi Interactions of Aromatics on the Surface of Single-Wall Carbon Nanotubes: An MP2 Study. J. Phys. Chem. C. 2008, 112, 20070–20075. DOI: 10.1021/jp807809u.
   Web of Science ®Google Scholar
• Wise, K. E.; Park, C.; Siochi, E. J.; Harrison, J. S. Stable Dispersion of Single Wall Carbon Nanotubes in Polyimide: The Role of Noncovalent Interactions. Chem. Phys. Lett. 2004, 391, 207–211. DOI: 10.1016/j.cplett.2004.04.096.
   Web of Science ®Google Scholar
• Lu, J.; Lai, L.; Luo, G.; Zhou, J.; Qin, R.; Wang, D.; Wang, L.; Mei, W. N.; Li, G.; Gao, Z.; et al. Why Semiconducting Single-Walled Carbon Nanotubes Are Separated from Their Metaltic Counterparts. Small 2007, 3, 1566–1576. DOI: 10.1002/smll.200700127.
   PubMed Web of Science ®Google Scholar