Journals / Hacettepe Journal of Biology and Chemistry / 2019 / Cilt: 47 - Sayı: 1

Evaluating the Reactivity Superiority of Two Different Single-Walled Carbon Nanotube Anions Using An Anhydride Electrophile

İki Farklı Tek Duvarlı Karbon Nanotüp Anyonunun Reaktivite Üstünlüğünün Bir Anhidrit Elektrofil Kullanarak Değerlendirilmesi

Pages
107–114
Publication Date
2022-10-17
DOI
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AI Summary & Key Takeaways

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⚡ TL;DR(Too Long; Didn't Read)

This isprobably due to the high nucleophilic character of [(nBu―SWCNTn)-•Lin+] which bears lone pair electrons and electrondonating butyl groups

📌 3 Key Takeaways

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Objective & Hypothesis:Reductive chemistries have widely been used to functionalize single-walled carbon nanotubes (SWCNTs).
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Key Findings & Data:Here in, the first example of the reactivity comparison of two differentNC-SWCNTs towards 3-nitrophthalic anhydride is presented, and two novel functionalized SWCNTs are synthesized andcharacterized.
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Conclusion & Impact:This isprobably due to the high nucleophilic character of [(nBu―SWCNTn)-•Lin+] which bears lone pair electrons and electrondonating butyl groups
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

Reductive chemistries have widely been used to functionalize single-walled carbon nanotubes (SWCNTs). However,the reactivity of negatively charged SWCNTs (NC-SWCNTs), prepared by different reductive chemistries, to the sameelectrophilic reagent has not been evaluated. Here in, the first example of the reactivity comparison of two differentNC-SWCNTs towards 3-nitrophthalic anhydride is presented, and two novel functionalized SWCNTs are synthesized andcharacterized. The NC-SWCNTs, that are denoted as [(nBu―SWCNTn)-•Lin+] and [SWCNTn-•Lin+], are prepared via n-butyllithium and lithium naphthalenide addition, respectively, and are reacted by 3-nitrophthalic anhydride under dry conditions.The resulting functionalized SWCNTs are characterized by Raman, UV-vis-NIR, TGA-MS, XPS, and TEM. The reactivity of[(nBu―SWCNTn)-•Lin+] towards electrophilic 3-nitrophthalic anhydride is found to be higher than [SWCNTn-•Lin+]. This isprobably due to the high nucleophilic character of [(nBu―SWCNTn)-•Lin+] which bears lone pair electrons and electrondonating butyl groups

Özet

İndirgenme kimyası tek duvarlı karbon nanotüpleri (TDKNT’ler) işlevselleştirmek için yaygın olarak kullanılmaktadır. Bugüne kadar, farklı indirgeyici kimyasallar tarafından hazırlanan negatif yüklü TDKNT’lerin (NY-TDKNT) elektrofilik reaktiflere karşı reaktivitesi değerlendirilmemiştir. Burada, iki farklı NY-TDKNT’nin 3-nitroftalik anhidrid’e karşı reaktivite karşılaştırmasının ilk örneği sunulmuştur ve iki yeni işlevselleştirilmiş TDKNT sentezlenmiş ve karakterize edilmiştir. Sırasıyla n-bütil lityum ve lityum naftalinit ilavesiyle hazırlanmış olan NY-TDKNT’ler ([(nBu― TDKNTn )- •Lin + ] ve [TDKNTn-•Lin + ]) kuru koşullar altında 3-nitroftalik anhidrit ile reaksiyona tabi tutulmuşlardır. Elde edilen işlevselleştirilmiş TDKNT’ler Raman, UV-vis-NIR, TGAMS ve TEM ile karakterize edilmiştir. [(nBu― TDKNTn )- •Lin + ]’nin 3-nitroftalik anhidrit elektrofile karşı reaktivitesinin [(nBu― TDKNTn )- •Lin + ]’den daha yüksek olduğu bulunmuştur. Bu muhtemelen yalnız bir elektron çifti ve elektron veren bütil grupları taşıyan [(nBu― TDKNTn )- •Lin ]’nin yüksek nükleofilik karakterinden kaynaklanmaktadır.

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Cite This Article

BAYAZİT, M. K. (2022). Evaluating the Reactivity Superiority of Two Different Single-Walled Carbon Nanotube Anions Using An Anhydride Electrophile. Hacettepe Journal of Biology and Chemistry, Cilt: 47 - Sayı: 1, 107–114. https://ajindex.com/articles/529030

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References (12)

  1. M.K. Bayazit, L.S. Clarke, K.S. Coleman, N. Clarke, Pyridinefunctionalized single-walled carbon nanotubes as gelators for poly(acrylic acid) hydrogels, J. Am. Chem. Soc., 132 (2010) 15814-15819
  2. M.K. Bayazit, K.S. Coleman, Fluorescent single-walled carbon nanotubes following the 1,3-dipolar cycloaddition of pyridinium ylides, J. Am. Chem. Soc., 131 (2009) 10670- 10676
  3. S.A. Hodge, M.K. Bayazit, K.S. Coleman, M.S.P. Shaffer, Unweaving the rainbow: a review of the relationship between single-walled carbon nanotube molecular structures and their chemical reactivity, Chem. Soc. Rev., 41 (2012) 4409-4429
  4. M.K. Bayazit, A. Suri, K.S. Coleman, Formylation of singlewalled carbon nanotubes, Carbon, 48 (2010) 3412-3419
  5. B. Gebhardt, Z. Syrgiannis, C. Backes, R. Graupner, F. Hauke, A. Hirsch, Carbon Nanotube sidewall functionalization with carbonyl compounds-modified birch conditions vs the organometallic reduction approach, J. Am. Chem. Soc., 133 (2011) 7985-7995
  6. M.K. Bayazit, K.S. Coleman, Ester-functionalized singlewalled carbon nanotubes via addition of haloformates, J. Material. Sci., 49 (2014) 5190-5198
  7. A.J. Clancy, J. Melbourne, M.S.P. Shaffer, A one-step route to solubilised, purified or functionalised single-walled carbon nanotubes, J. Mater. Chem. A, 3 (2015) 16708-16715
  8. M. De Marco, F. Markoulidis, R. Menzel, S.M. Bawaked, M. Mokhtar, S.A. Al-Thabaiti, S.N. Basahel, M.S.P. Shaffer, Crosslinked single-walled carbon nanotube aerogel electrodes via reductive coupling chemistry, J. Mater. Chem. A, 4 (2016) 5385-5389.9. G. Viswanathan, N. Chakrapani, H.C. Yang, B.Q. Wei, H.S. Chung, K.W. Cho, C.Y. Ryu, P.M. Ajayan, Single-step in situ synthesis of polymer-grafted single-wall nanotube composites, J. Am. Chem. Soc., 125 (2003) 9258-9259
  9. R. Blake, Y.K. Gun’ko, J. Coleman, M. Cadek, A. Fonseca, J.B. Nagy, W.J. Blau, A generic organometallic approach toward ultra-strong carbon nanotube polymer composites, J. Am. Chem. Soc., 126 (2004) 10226-10227
  10. S. Chen, W. Shen, G. Wu, D. Chen, M. Jiang, A new approach to the functionalization of single-walled carbon nanotubes with both alkyl and carboxyl groups, Chem. Phys. Lett., 402 (2005) 312-317
  11. S. Pekker, J.P. Salvetat, E. Jakab, J.M. Bonard, L. Forró, Hydrogenation of carbon nanotubes and graphite in liquid ammonia, J. Phys. Chem. B, 105 (2001) 7938-7943
  12. A. Pénicaud, P. Poulin, A. Derré, E. Anglaret, P. Petit, Spontaneous dissolution of a single-wall carbon nanotube salt, J. Am