Functionalization: Tailoring nanocarbons through attached molecules and particles
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1 Functionalization: Tailoring nanocarbons through attached molecules and particles Gabriel Kabbe Supervisor: Pascal Blümmel 1
2 Why functionalizing nanotubes?
3 Different forms of functionalization Endohedral functionalization 3
4 Covalent functionalization P.Blümmel:Solubilization and Individualization of Carbon Nanotubes by Noncovalent Functionalization with Switchable Molecules 4
5 Covalent functionalization 5
6 Covalent functionalization CNT oxidation and Carboxyl-based couplings Electro Chemical Modification Photochemical functionalization Balasubramanian, Burghard: Chemically Functionalized Carbon Nanotubes 6
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 7
8 Covalent bonding Disadvantage: mechanical and electronic properties are changed!! 8
9 Non-covalent bonding non-destructive π-π-interaction and/or van-der Waals interaction examples: e) DDQ (2,3,-dichloro-5,6-dicyano-1,4benzoquinone) Picture:Hirsch, Vostrowsky Functionalization of Carbon Nanotubes Springer-Verlag 2005 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 9
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 10
11 Functionalization with switches Picture: P.Blümmel:Solubilization and Individualization of Carbon Nanotubes by Noncovalent Functionalization with Switchable Molecules 11
12 Functionalization with switches Retinal (11-cis and all-trans) 12
13 Functionalization with switches Picture: P.Blümmel:Solubilization and Individualization of Carbon Nanotubes by Noncovalent Functionalization with Switchable Molecules 13
14 Functionalization with switches Spiropyran Merocyanin Picture: P.Blümmel:Solubilization and Individualization of Carbon Nanotubes by Noncovalent Functionalization with Switchable Molecules 14
15 Functionalization with switches Example: Spiropyran non-covalently connected to semiconducting nanotubes FET: Source Drain 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 15
16 Functionalization with antibodies absorbance spectrum 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 16
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 17
18 Polymer wrapping 18
19 Polymer wrapping Application: Chirality enrichment Rational Concept To Recognize/Extract Single-Walled Carbon Nanotubes with a Specific Chirality Hiroaki Ozawa,Tsuyohiko Fujigaya 19
20 Polymer wrapping Rational Concept To Recognize/Extract Single-Walled Carbon Nanotubes with a Specific Chirality Hiroaki Ozawa,Tsuyohiko Fujigaya copolymer: 20
21 Endohedral functionalization P.Blümmel:Solubilization and Individualization of Carbon Nanotubes by Noncovalent Functionalization with Switchable Molecules 21
22 Endohedral functionalization 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 Chen et al. Carbon-Nanotube-Based Stimuli-Responsive Controlled-Release System 22
23 Endohedral functionalization TEM images: Silica sphere Opened CNT Closed CNT 23
24 Summary Covalent Non-covalent Destroys Carbon framework Leaves CNT intact Reversible Endohedral Uses CNT's weak reactivity inside Irreversible Polymer wrapping Chirality selection 24
25 Thank you!!! 25
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 26
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