Skip to main content
Erschienen in: Journal of Materials Science 14/2014

01.07.2014

Ester-functionalized single-walled carbon nanotubes via addition of haloformates

verfasst von: Mustafa K. Bayazit, Karl S. Coleman

Erschienen in: Journal of Materials Science | Ausgabe 14/2014

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Herein, a versatile method to introduce ester functional groups to the surface of single-walled carbon nanotubes (SWCNTs) was defined. Ester-modified SWCNTs were prepared via the direct reaction of haloformates with reduced SWCNTs [(nBuSWCNT n ) Li n + ] generated by n-butyl lithium. Ultraviolet–Visible–near infrared and Raman spectroscopy verified the evidence of covalent surface functionalization. Solubility of functionalized SWCNTs (f-SWCNTs) enhanced compared to purified SWCNTs. Gold tagging to positively charged SWCNTs displayed the presence and distribution of functional groups, confirming the conversion of esters into amides. f-SWCNTs were further characterized by thermo-gravimetric analysis coupled with mass spectrometry and fourier-transform infrared spectroscopy.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Anhänge
Nur mit Berechtigung zugänglich
Literatur
1.
Zurück zum Zitat Hodge SA, Bayazit MK, Coleman KS, Shaffer MSP (2012) Unweaving the rainbow: a review of the relationship between single-walled carbon nanotube molecular structures and their chemical reactivity. Chem Soc Rev 41(12):4409–4429. doi:10.1039/c2cs15334c CrossRef Hodge SA, Bayazit MK, Coleman KS, Shaffer MSP (2012) Unweaving the rainbow: a review of the relationship between single-walled carbon nanotube molecular structures and their chemical reactivity. Chem Soc Rev 41(12):4409–4429. doi:10.​1039/​c2cs15334c CrossRef
2.
Zurück zum Zitat Bahr JL, Yang JP, Kosynkin DV, Bronikowski MJ, Smalley RE, Tour JM (2001) Functionalization of carbon nanotubes by electrochemical reduction of aryl diazonium salts: a bucky paper electrode. J Am Chem Soc 123(27):6536–6542. doi:10.1021/ja010462s CrossRef Bahr JL, Yang JP, Kosynkin DV, Bronikowski MJ, Smalley RE, Tour JM (2001) Functionalization of carbon nanotubes by electrochemical reduction of aryl diazonium salts: a bucky paper electrode. J Am Chem Soc 123(27):6536–6542. doi:10.​1021/​ja010462s CrossRef
4.
5.
8.
11.
Zurück zum Zitat Bayazit MK, Clarke LS, Coleman KS, Clarke N (2010) Pyridine-functionalized single-walled carbon nanotubes as gelators for poly(acrylic acid) hydrogels. J Am Chem Soc 132(44):15814–15819. doi:10.1021/ja1076662 CrossRef Bayazit MK, Clarke LS, Coleman KS, Clarke N (2010) Pyridine-functionalized single-walled carbon nanotubes as gelators for poly(acrylic acid) hydrogels. J Am Chem Soc 132(44):15814–15819. doi:10.​1021/​ja1076662 CrossRef
12.
Zurück zum Zitat Bayazit MK, Coleman KS (2012) Probing the selectivity of azomethine imine cycloaddition to single-walled carbon nanotubes by resonance Raman spectroscopy. Chem Asian J 7(12):2925–2930. doi:10.1002/asia.201200714 CrossRef Bayazit MK, Coleman KS (2012) Probing the selectivity of azomethine imine cycloaddition to single-walled carbon nanotubes by resonance Raman spectroscopy. Chem Asian J 7(12):2925–2930. doi:10.​1002/​asia.​201200714 CrossRef
13.
Zurück zum Zitat Bayazit MK, Coleman KS (2009) Fluorescent single-walled carbon nanotubes following the 1,3-dipolar cycloaddition of pyridinium ylides. J Am Chem Soc 131(30):10670–10676. doi:10.1021/ja903712f CrossRef Bayazit MK, Coleman KS (2009) Fluorescent single-walled carbon nanotubes following the 1,3-dipolar cycloaddition of pyridinium ylides. J Am Chem Soc 131(30):10670–10676. doi:10.​1021/​ja903712f CrossRef
16.
Zurück zum Zitat Tans SJ, Verschueren ARM, Dekker C (1998) Room-temperature transistor based on a single carbon nanotube. Nature 393(6680):49–52CrossRef Tans SJ, Verschueren ARM, Dekker C (1998) Room-temperature transistor based on a single carbon nanotube. Nature 393(6680):49–52CrossRef
18.
Zurück zum Zitat Dai HJ, Hafner JH, Rinzler AG, Colbert DT, Smalley RE (1996) Nanotubes as nanoprobes in scanning probe microscopy. Nature 384(6605):147–150. doi:10.1038/384147a0 CrossRef Dai HJ, Hafner JH, Rinzler AG, Colbert DT, Smalley RE (1996) Nanotubes as nanoprobes in scanning probe microscopy. Nature 384(6605):147–150. doi:10.​1038/​384147a0 CrossRef
19.
Zurück zum Zitat Wong SS, Joselevich E, Woolley AT, Cheung CL, Lieber CM (1998) Covalently functionalized nanotubes as nanometre-sized probes in chemistry and biology. Nature 394(6688):52–55CrossRef Wong SS, Joselevich E, Woolley AT, Cheung CL, Lieber CM (1998) Covalently functionalized nanotubes as nanometre-sized probes in chemistry and biology. Nature 394(6688):52–55CrossRef
20.
Zurück zum Zitat Baughman RH, Cui CX, Zakhidov AA, Iqbal Z, Barisci JN, Spinks GM, Wallace GG, Mazzoldi A, De Rossi D, Rinzler AG, Jaschinski O, Roth S, Kertesz M (1999) Carbon nanotube actuators. Science 284(5418):1340–1344. doi:10.1126/science.284.5418.1340 CrossRef Baughman RH, Cui CX, Zakhidov AA, Iqbal Z, Barisci JN, Spinks GM, Wallace GG, Mazzoldi A, De Rossi D, Rinzler AG, Jaschinski O, Roth S, Kertesz M (1999) Carbon nanotube actuators. Science 284(5418):1340–1344. doi:10.​1126/​science.​284.​5418.​1340 CrossRef
21.
Zurück zum Zitat Dillon AC, Jones KM, Bekkedahl TA, Kiang CH, Bethune DS, Heben MJ (1997) Storage of hydrogen in single-walled carbon nanotubes. Nature 386(6623):377–379. doi:10.1038/386377a0 CrossRef Dillon AC, Jones KM, Bekkedahl TA, Kiang CH, Bethune DS, Heben MJ (1997) Storage of hydrogen in single-walled carbon nanotubes. Nature 386(6623):377–379. doi:10.​1038/​386377a0 CrossRef
23.
Zurück zum Zitat Choi WB, Chung DS, Kang JH, Kim HY, Jin YW, Han IT, Lee YH, Jung JE, Lee NS, Park GS, Kim JM (1999) Fully sealed, high-brightness carbon-nanotube field-emission display. Appl Phys Lett 75(20):3129–3131. doi:10.1063/1.125253 CrossRef Choi WB, Chung DS, Kang JH, Kim HY, Jin YW, Han IT, Lee YH, Jung JE, Lee NS, Park GS, Kim JM (1999) Fully sealed, high-brightness carbon-nanotube field-emission display. Appl Phys Lett 75(20):3129–3131. doi:10.​1063/​1.​125253 CrossRef
24.
Zurück zum Zitat Cooper EB, Manalis SR, Fang H, Dai H, Matsumoto K, Minne SC, Hunt T, Quate CF (1999) Terabit-per-square-inch data storage with the atomic force microscope. Appl Phys Lett 75(22):3566–3568. doi:10.1063/1.125390 CrossRef Cooper EB, Manalis SR, Fang H, Dai H, Matsumoto K, Minne SC, Hunt T, Quate CF (1999) Terabit-per-square-inch data storage with the atomic force microscope. Appl Phys Lett 75(22):3566–3568. doi:10.​1063/​1.​125390 CrossRef
26.
Zurück zum Zitat Gebhardt B, Syrgiannis Z, Backes C, Graupner R, Hauke F, Hirsch A (2011) Carbon nanotube sidewall functionalization with carbonyl compounds-modified birch conditions vs the organometallic reduction approach. J Am Chem Soc 133(20):7985–7995. doi:10.1021/ja2016872 CrossRef Gebhardt B, Syrgiannis Z, Backes C, Graupner R, Hauke F, Hirsch A (2011) Carbon nanotube sidewall functionalization with carbonyl compounds-modified birch conditions vs the organometallic reduction approach. J Am Chem Soc 133(20):7985–7995. doi:10.​1021/​ja2016872 CrossRef
27.
Zurück zum Zitat Hof F, Bosch S, Eigler S, Hauke F, Hirsch A (2013) New basic insight into reductive functionalization sequences of single walled carbon nanotubes (SWCNTs). J Am Chem Soc 135(49):18385–18395. doi:10.1021/ja4063713 CrossRef Hof F, Bosch S, Eigler S, Hauke F, Hirsch A (2013) New basic insight into reductive functionalization sequences of single walled carbon nanotubes (SWCNTs). J Am Chem Soc 135(49):18385–18395. doi:10.​1021/​ja4063713 CrossRef
29.
Zurück zum Zitat Lee R-H, Lee L-Y, Huang J-L, Huang C-C, Hwang J-C (2011) Conjugated polymer-functionalized carbon nanotubes enhance the photovoltaic properties of polymer solar cells. Colloid Polym Sci 289(15–16):1633–1641. doi:10.1007/s00396-011-2481-1 CrossRef Lee R-H, Lee L-Y, Huang J-L, Huang C-C, Hwang J-C (2011) Conjugated polymer-functionalized carbon nanotubes enhance the photovoltaic properties of polymer solar cells. Colloid Polym Sci 289(15–16):1633–1641. doi:10.​1007/​s00396-011-2481-1 CrossRef
30.
Zurück zum Zitat Zydziak N, Preuss CM, Winkler V, Bruns M, Huebner C, Barner-Kowollik C (2013) Hetero diels-alder chemistry for the functionalization of single-walled carbon nanotubes with cyclopentadienyl end-capped polymer strands. Macromol Rapid Commun 34(8):672–680. doi:10.1002/marc.201300025 CrossRef Zydziak N, Preuss CM, Winkler V, Bruns M, Huebner C, Barner-Kowollik C (2013) Hetero diels-alder chemistry for the functionalization of single-walled carbon nanotubes with cyclopentadienyl end-capped polymer strands. Macromol Rapid Commun 34(8):672–680. doi:10.​1002/​marc.​201300025 CrossRef
31.
Zurück zum Zitat Itkis ME, Perea DE, Jung R, Niyogi S, Haddon RC (2005) Comparison of analytical techniques for purity evaluation of single-walled carbon nanotubes. J Am Chem Soc 127(10):3439–3448. doi:10.1021/ja043061w CrossRef Itkis ME, Perea DE, Jung R, Niyogi S, Haddon RC (2005) Comparison of analytical techniques for purity evaluation of single-walled carbon nanotubes. J Am Chem Soc 127(10):3439–3448. doi:10.​1021/​ja043061w CrossRef
32.
Zurück zum Zitat Strano MS, Huffman CB, Moore VC, O’Connell MJ, Haroz EH, Hubbard J, Miller M, Rialon K, Kittrell C, Ramesh S, Hauge RH, Smalley RE (2003) Reversible, band-gap-selective protonation of single-walled carbon nanotubes in solution. J Phys Chem B 107(29):6979–6985. doi:10.1021/jp027664a CrossRef Strano MS, Huffman CB, Moore VC, O’Connell MJ, Haroz EH, Hubbard J, Miller M, Rialon K, Kittrell C, Ramesh S, Hauge RH, Smalley RE (2003) Reversible, band-gap-selective protonation of single-walled carbon nanotubes in solution. J Phys Chem B 107(29):6979–6985. doi:10.​1021/​jp027664a CrossRef
33.
Zurück zum Zitat Li Q, Li Y, Zhang X, Chikkannanavar SB, Zhao Y, Dangelewicz AM, Zheng L, Doorn SK, Jia Q, Peterson DE, Arendt PN, Zhu Y (2007) Structure-dependent electrical properties of carbon nanotube fibers. Adv Mater 19(20):3358–3363. doi:10.1002/adma.200602966 CrossRef Li Q, Li Y, Zhang X, Chikkannanavar SB, Zhao Y, Dangelewicz AM, Zheng L, Doorn SK, Jia Q, Peterson DE, Arendt PN, Zhu Y (2007) Structure-dependent electrical properties of carbon nanotube fibers. Adv Mater 19(20):3358–3363. doi:10.​1002/​adma.​200602966 CrossRef
34.
Zurück zum Zitat Darabi HR, Roozkhosh A, Tehrani MJ, Aghapoor K, Sayahi H, Balavar Y, Mohsenzadeh F (2014) Characterization of ester- or thioamide-functionalized single-walled carbon nanotube-azithromycin conjugates. Appl Surf Sci 288:122–129. doi:10.1016/j.apsusc.2013.09.159 CrossRef Darabi HR, Roozkhosh A, Tehrani MJ, Aghapoor K, Sayahi H, Balavar Y, Mohsenzadeh F (2014) Characterization of ester- or thioamide-functionalized single-walled carbon nanotube-azithromycin conjugates. Appl Surf Sci 288:122–129. doi:10.​1016/​j.​apsusc.​2013.​09.​159 CrossRef
35.
Zurück zum Zitat Reed MW, Moore HW (1988) Efficient synthesis of furochromone and furocoumarin natural-products (khellin, pimpinellin, isophellopterin) by thermal rearrangement of 4-furyl-4-hydroxycyclobutenones. J Org Chem 53(18):4166–4171. doi:10.1021/jo00253a002 CrossRef Reed MW, Moore HW (1988) Efficient synthesis of furochromone and furocoumarin natural-products (khellin, pimpinellin, isophellopterin) by thermal rearrangement of 4-furyl-4-hydroxycyclobutenones. J Org Chem 53(18):4166–4171. doi:10.​1021/​jo00253a002 CrossRef
36.
Zurück zum Zitat Graupner R, Abraham J, Wunderlich D, Vencelova A, Lauffer P, Roehrl J, Hundhausen M, Ley L, Hirsch A (2006) Nucleophilic-alkylation-reoxidation: a functionalization sequence for single-wall carbon nanotubes. J Am Chem Soc 128(20):6683–6689. doi:10.1021/ja0607281 CrossRef Graupner R, Abraham J, Wunderlich D, Vencelova A, Lauffer P, Roehrl J, Hundhausen M, Ley L, Hirsch A (2006) Nucleophilic-alkylation-reoxidation: a functionalization sequence for single-wall carbon nanotubes. J Am Chem Soc 128(20):6683–6689. doi:10.​1021/​ja0607281 CrossRef
37.
Zurück zum Zitat Wunderlich D, Hauke F, Hirsch A (2008) Preferred functionalization of metallic and small-diameter single-walled carbon nanotubes by nucleophilic addition of organolithium and -magnesium compounds followed by reoxidation. Chem Eur J 14(5):1607–1614. doi:10.1002/chem.200701038 CrossRef Wunderlich D, Hauke F, Hirsch A (2008) Preferred functionalization of metallic and small-diameter single-walled carbon nanotubes by nucleophilic addition of organolithium and -magnesium compounds followed by reoxidation. Chem Eur J 14(5):1607–1614. doi:10.​1002/​chem.​200701038 CrossRef
38.
Zurück zum Zitat Landi BJ, Ruf HJ, Worman JJ, Raffaelle RP (2004) Effects of alkyl amide solvents on the dispersion of single-wall carbon nanotubes. J Phys Chem B 108(44):17089–17095. doi:10.1021/jp047521j CrossRef Landi BJ, Ruf HJ, Worman JJ, Raffaelle RP (2004) Effects of alkyl amide solvents on the dispersion of single-wall carbon nanotubes. J Phys Chem B 108(44):17089–17095. doi:10.​1021/​jp047521j CrossRef
39.
Zurück zum Zitat Banerjee S, Wong SS (2004) Demonstration of diameter-selective reactivity in the sidewall ozonation of SWNTs by resonance Raman spectroscopy. Nano Lett 4(8):1445–1450. doi:10.1021/nl049261n CrossRef Banerjee S, Wong SS (2004) Demonstration of diameter-selective reactivity in the sidewall ozonation of SWNTs by resonance Raman spectroscopy. Nano Lett 4(8):1445–1450. doi:10.​1021/​nl049261n CrossRef
40.
Zurück zum Zitat Brown SDM, Jorio A, Corio P, Dresselhaus MS, Dresselhaus G, Saito R, Kneipp K (2001) Origin of the Breit–Wigner–Fano lineshape of the tangential G-band feature of metallic carbon nanotubes. Phys Rev B 63(15):155414. doi:10.1103/PhysRevB.63.155414 CrossRef Brown SDM, Jorio A, Corio P, Dresselhaus MS, Dresselhaus G, Saito R, Kneipp K (2001) Origin of the Breit–Wigner–Fano lineshape of the tangential G-band feature of metallic carbon nanotubes. Phys Rev B 63(15):155414. doi:10.​1103/​PhysRevB.​63.​155414 CrossRef
41.
Zurück zum Zitat Kukovecz A, Pichler T, Pfeiffer R, Kramberger C, Kuzmany H (2003) Diameter selective doping of single wall carbon nanotubes. Phys Chem Chem Phys 5(3):582–587. doi:10.1039/b211509c CrossRef Kukovecz A, Pichler T, Pfeiffer R, Kramberger C, Kuzmany H (2003) Diameter selective doping of single wall carbon nanotubes. Phys Chem Chem Phys 5(3):582–587. doi:10.​1039/​b211509c CrossRef
42.
Zurück zum Zitat Strano MS (2003) Probing chiral selective reactions using a revised Kataura plot for the interpretation of single-walled carbon nanotube spectroscopy. J Am Chem Soc 125(51):16148–16153. doi:10.1021/ja036791x CrossRef Strano MS (2003) Probing chiral selective reactions using a revised Kataura plot for the interpretation of single-walled carbon nanotube spectroscopy. J Am Chem Soc 125(51):16148–16153. doi:10.​1021/​ja036791x CrossRef
43.
Zurück zum Zitat Heaps DA, Griffiths PR (2005) Reduction of detection limits of the direct deposition GC/FT-IR interface by surface-enhanced infrared absorption. Anal Chem 77(18):5965–5972. doi:10.1021/ac050585I CrossRef Heaps DA, Griffiths PR (2005) Reduction of detection limits of the direct deposition GC/FT-IR interface by surface-enhanced infrared absorption. Anal Chem 77(18):5965–5972. doi:10.​1021/​ac050585I CrossRef
44.
Zurück zum Zitat Basiuk EV, Monroy-Pelaez M, Puente-Lee I, Basiuk VA (2004) Direct solvent-free amination of closed-cap carbon nanotubes: a link to fullerene chemistry. Nano Lett 4(5):863–866. doi:10.1021/nl049746b CrossRef Basiuk EV, Monroy-Pelaez M, Puente-Lee I, Basiuk VA (2004) Direct solvent-free amination of closed-cap carbon nanotubes: a link to fullerene chemistry. Nano Lett 4(5):863–866. doi:10.​1021/​nl049746b CrossRef
45.
Zurück zum Zitat Jombert AS, Bayazit MK, Herron CR, Coleman KS, Zeze DA (2013) Synthesis and characterization of molecularly-bridged single-walled carbon nanotubes and electrical properties of their films. Sci Adv Mater 5(12):1967–1973. doi:10.1166/sam.2013.1664 CrossRef Jombert AS, Bayazit MK, Herron CR, Coleman KS, Zeze DA (2013) Synthesis and characterization of molecularly-bridged single-walled carbon nanotubes and electrical properties of their films. Sci Adv Mater 5(12):1967–1973. doi:10.​1166/​sam.​2013.​1664 CrossRef
Metadaten
Titel
Ester-functionalized single-walled carbon nanotubes via addition of haloformates
verfasst von
Mustafa K. Bayazit
Karl S. Coleman
Publikationsdatum
01.07.2014
Verlag
Springer US
Erschienen in
Journal of Materials Science / Ausgabe 14/2014
Print ISSN: 0022-2461
Elektronische ISSN: 1573-4803
DOI
https://doi.org/10.1007/s10853-014-8227-y

Weitere Artikel der Ausgabe 14/2014

Journal of Materials Science 14/2014 Zur Ausgabe

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.