Functionalization: Tailoring nanocarbons through attached molecules - - PowerPoint PPT Presentation

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Functionalization: Tailoring nanocarbons through attached molecules - - PowerPoint PPT Presentation

Dec 29, 2022 422 likes •707 views

Functionalization: Tailoring nanocarbons through attached molecules and particles Gabriel Kabbe Supervisor: Pascal Blmmel Functionalization of CNT, Datum, ... 1 Why functionalizing nanotubes?

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Functionalization of CNT, Datum, ... 1

Functionalization: Tailoring nanocarbons through attached molecules and particles

Gabriel Kabbe Supervisor: Pascal Blümmel

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Functionalization of CNT, Datum, ... 2

Why functionalizing nanotubes?

http://www.nanotech-now.com/images/Infineon-nanotube.jpg

http://www.cen-der-blog.de/wordpress/wp-content/uploads/2009/08/Wassertropfen.jpg

http://www.ricercaitaliana.it/images/rif/PRIN/2004035502/imm_0001.jpg

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Functionalization of CNT, Datum, ... 3

Different forms of functionalization

http://www.jmtour.com/images/Nanotubes/NanotubeFunctionalizationLiBottomStyreneTop.jpg http://www.nanotech-now.com/images/nanohydraulic-piston-large.jpg

Endohedral functionalization

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Functionalization of CNT, Datum, ... 4

Covalent functionalization

P.Blümmel:Solubilization and Individualization

  • f Carbon Nanotubes by Noncovalent Functionalization

with Switchable Molecules

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Functionalization of CNT, Datum, ... 5

Covalent functionalization

http://www.cup.uni-muenchen.de/ac/kluefers/homepage/L/gp/gp_bunsenbrenner_entleuchtet_96.gif http://upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Elektrolyse_Allgemein.jpg/621px-Elektrolyse_Allgemein.jpg

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Functionalization of CNT, Datum, ... 6

Covalent functionalization

  • CNT oxidation and Carboxyl-based couplings
  • Electro Chemical Modification
  • Photochemical functionalization

Balasubramanian, Burghard: Chemically Functionalized Carbon Nanotubes

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Functionalization of CNT, Datum, ... 7

Covalent functionalization

Applications:

  • hydrogen sensor
  • semiconducting nanotube is covered

with Pd layer

  • H2 is split into H+ by Pd

→ charge-carrier concentration of SWCNT is changed → electrical resistance changes

Balasubramanian, Burghard: Chemically Functionalized Carbon Nanotubes

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Functionalization of CNT, Datum, ... 8

Covalent bonding

Disadvantage: → mechanical and electronic properties are changed!!

http://homepage.mac.com/jhgowen/research/nanotube_page/nanotube.jpg

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Functionalization of CNT, Datum, ... 9

Non-covalent bonding

  • non-destructive
  • π-π-interaction and/or van-der Waals interaction
  • examples:

e) DDQ (2,3,-dichloro-5,6-dicyano-1,4- benzoquinone) f)Pyrene

Tasis, Chemistry of Carbon Nanotubes (Chem.Rev.2006)

Picture: P.Blümmel:Solubilization and Individualization of

  • Carbon Nanotubes by Noncovalent Functionalization

with Switchable Molecules

Picture:Hirsch, Vostrowsky Functionalization of Carbon Nanotubes Springer-Verlag 2005

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Functionalization of CNT, Datum, ... 10

π-π-interaction (Hunter-Sanders-Model)

a) group charges of an atom into π- electrons (negative charge) and core plus σ-electrons (positive charge) b)attraction/repulsion depends on relative angle and offset between two atoms

Christopher A. Hunter, Jeremy K. M. Sanders The Nature of π-π Interactions

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Functionalization of CNT, Datum, ... 11

Functionalization with switches

Picture: P.Blümmel:Solubilization and Individualization of

  • Carbon Nanotubes by Noncovalent Functionalization

with Switchable Molecules

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Functionalization of CNT, Datum, ... 12

Functionalization with switches

Retinal (11-cis and all-trans)

http://upload.wikimedia.org/wikipedia/commons/thumb/1/11/RetinalCisandTrans.png/800px-RetinalCisandTrans.png

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Functionalization of CNT, Datum, ... 13

Functionalization with switches

Picture: P.Blümmel:Solubilization and Individualization of

  • Carbon Nanotubes by Noncovalent Functionalization

with Switchable Molecules

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Functionalization of CNT, Datum, ... 14

Functionalization with switches

Spiropyran ↔ Merocyanin

Picture: P.Blümmel:Solubilization and Individualization of

  • Carbon Nanotubes by Noncovalent Functionalization

with Switchable Molecules

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Functionalization of CNT, Datum, ... 15

Functionalization with switches

Example: Spiropyran non-covalently connected to semiconducting nanotubes

Directing and Sensing Changes in Molecular Conformation on Individual Carbon Nanotube Field Effect Transistors Xuefeng Guo, Limin Huang, Stephen O’Brien, Philip Kim,* and Colin Nuckolls

Source Drain FET:

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Functionalization of CNT, Datum, ... 16

Functionalization with antibodies

Integrated molecular targeting of IGF1R and HER2 surface receptors and

destruction of breast cancer cells using single wall carbon nanotubes Ning Shao, Shaoxin Lu, EricWickstrom2 and Balaji Panchapakesan1

absorbance spectrum

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Functionalization of CNT, Datum, ... 17

Functionalization with antibodies

NIR (near-infrared) without nanotube + antibody NIR with nanotube + antibody Integrated molecular targeting of IGF1R and HER2 surface receptors and

destruction of breast cancer cells using single wall carbon nanotubes Ning Shao, Shaoxin Lu, EricWickstrom2 and Balaji Panchapakesan1

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Functionalization of CNT, Datum, ... 18

Polymer wrapping

http://www.nanotech-now.com/images/Art_Gallery/Accelrys-helical-wrap-large.jpg

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Functionalization of CNT, Datum, ... 19

Polymer wrapping

Application: Chirality enrichment

Rational Concept To Recognize/Extract Single-Walled Carbon Nanotubes with a Specific Chirality Hiroaki Ozawa,Tsuyohiko Fujigaya

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Functionalization of CNT, Datum, ... 20

Polymer wrapping

copolymer:

Rational Concept To Recognize/Extract Single-Walled Carbon Nanotubes with a Specific Chirality Hiroaki Ozawa,Tsuyohiko Fujigaya

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Functionalization of CNT, Datum, ... 21

Endohedral functionalization

P.Blümmel:Solubilization and Individualization

  • f Carbon Nanotubes by Noncovalent Functionalization

with Switchable Molecules

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Functionalization of CNT, Datum, ... 22

Endohedral functionalization

Chen et al. Carbon-Nanotube-Based Stimuli-Responsive Controlled-Release System

„Filling“ a tube:

  • heat/oxidation process → open tube ends and

Introduce carboxyl groups at the openings

  • S-(2-aminoethylthio)-2-thiopyridine + CNT-COOH → CNT-S-S-Py
  • Tubes are filled with fluorescein
  • Thiol-silica nanospheres close the tubes
  • Reopen by heating or via reducing agents
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Functionalization of CNT, Datum, ... 23

Endohedral functionalization

TEM images: Opened CNT Silica sphere Closed CNT

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Functionalization of CNT, Datum, ... 24

Summary

Covalent

  • Destroys Carbon

framework

  • Irreversible

Non-covalent

  • Leaves CNT intact
  • Reversible

Endohedral

  • Uses CNT's

weak reactivity inside Polymer wrapping

  • Chirality selection
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Functionalization of CNT, Datum, ... 25

Thank you!!!

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Functionalization of CNT, Datum, ... 26

References

  • P.Blümmel:Solubilization and Individualization of Carbon Nanotubes by Noncovalent Functionalization

with Switchable Molecules

  • Balasubramanian, Burghard: Functionalization of Carbon Nanotubes
  • Tasis, Chemistry of Carbon Nanotubes (Chem.Rev.2006)
  • Hirsch, Vostrowsky Functionalization of Carbon Nanotubes Springer-Verlag 2005
  • Christopher A. Hunter, Jeremy K. M. SandersThe Nature of π-π Interactions
  • Guo et al. Directing and Sensing Changes in Molecular Conformation on Individual Carbon Nanotube Field

Effect Transistors (2005)

  • Shao et al. Integrated molecular targeting of IGF1R and HER2 surface receptors and

destruction of breast cancer cells using single wall carbon nanotubes

  • Ozawa et al. Rational Concept To Recognize/Extract Single-Walled Carbon Nanotubes with a Specific

Chirality

  • Chen et al. Carbon-Nanotube-Based Stimuli-Responsive Controlled-Release System