Domino Reaction for the Controlled Functionalization of sp 2 Carbon Allotropes
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1 Workshop AICIng Milano, June, 2017 Domino Reaction for the Controlled Functionalization of sp 2 Carbon Allotropes Vincenzina Barbera Alberto Milani, Luigi Brambilla, Chiara Castiglioni, Maurizio Galimberti vincenzina.barbera@polimi.it Politecnico di Milano, Department of Chemistry, Materials and Chemical Engineering G. Natta Innovative Sustainable Chemistry and Materials and Proteomics Group 1 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
2 Chemistry from biobased C-3 platform 2 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
3 Chemistry from biobased C-3 platform Yield: at least 96% Atom efficiency: 85% Easy procedure No solvent By product: H 2 O V. Barbera, A. Citterio, M. Galimberti, G. Leonardi, R. Sebastiano, S.U. Shisodia, A.M. Valerio. WO/2015/ A1 (2015) 3 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
4 Serinolpyrrole: Janus molecule INTERACTION WITH GRAPHITIC CARBONS INTERACTION WITH POLAR SURROUNDING 4 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
5 Carbon fillers from a layer of sp 2 -bonded carbon atoms graphene stacked wrapped randomly arranged stacked graphene layers with different shape anisotropy CNT carbon black graphite, nano-graphite, graphene 5 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
6 Characterization of carbon allotropes (CA) CB CNT FEW LAYERS GRAPHENE 6 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
7 Characterization of carbon allotropes (CA) CB TGA, Elemental Analysis: carbon purity BET: surface area, activity CNT Infrared, XPS: functional groups Raman, X-ray: bulk structure FEW LAYERS GRAPHENE 7 TEM, HRTEM: morphology V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
8 Facile functionalization of carbon materials Carbon allotrope Mixing, energy, air Oxygenated functional groups on carbon allotrope surface Bulk structure substantially unaltered M. Galimberti, V. Barbera, R. Sebastiano, A. Citterio, G. Leonardi, A.M. Valerio. WO/2016/ A1 (2016) 8 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
9 Facile functionalization of carbon materials Carbon allotrope Mixing, energy, air Oxygenated functional groups on carbon allotrope surface Bulk structure substantially unaltered M. Galimberti, V. Barbera, R. Sebastiano, A. Citterio, G. Leonardi, A.M. Valerio. WO/2016/ A1 (2016) 9 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
10 High yield functionalization! Yield: BET Surface area: 86 % 97 % 98 % 77 m 2 /g 275 m 2 /g 300 m 2 /g 10 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
11 High yield functionalization! Yield: BET Surface area: 86 % 97 % 98 % 77 m 2 /g 275 m 2 /g 300 m 2 /g High surface area graphite HSAG water suspensions from 1 to 0.01 mg/ml HSAG 11 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
12 Mechanistic investigation H 3 C H 3 C N CH 3 Model compound 12 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
13 Mechanistic investigation H 3 C H 3 C N CH 3 Model compound H 3 C N CH 3 H 3 C N CH 3 + HSAG H 3 C H 3 C In air In air Thermal energy Thermal energy 13 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
14 1,2,5-Trimethylpyrrole (TMP) C=C stretching cyclic alkene out of plane C-H bending Absorbance (a.u.) 25 C Wavenumbers (cm -1 ) V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
15 TMP from 25 to 150 C Δ Air C=C stretching cyclic alkene out of plane C-H bending Absorbance (a.u.) 150 C 130 C 80 C 25 C Increasing temperature Wavenumbers (cm -1 ) V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
16 TMP + HSAG cat. - from 25 to 150 C Δ, Air HSAG as cat. C=C stretching cyclic alkene out of plane C-H bending Absorbance (a.u.) TMP+HSAG 1% 80 C Increasing temperature TMP Wavenumbers (cm -1 ) 16 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
17 TMP + HSAG cat. - from 25 to 150 C Δ, Air HSAG as cat. C=C stretching cyclic alkene out of plane C-H bending Oxidation Absorbance (a.u.) TMP+HSAG 1% 130 C TMP+HSAG 1% 100 C TMP+HSAG 1% 80 C Increasing temperature TMP Wavenumbers (cm -1 ) 17 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
18 TMP + HSAG cat. - from 25 to 150 C Δ, Air HSAG as cat. C=C stretching cyclic alkene out of plane C-H bending Oxidation Absorbance (a.u.) TMP+HSAG 1% 150 C TMP+HSAG 1% 130 C TMP+HSAG 1% 100 C TMP+HSAG 1% 80 C Increasing temperature TMP Wavenumbers (cm -1 ) 18 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
19 TMP + HSAG 1/1 - from 25 to 150 C +HSAG Δ Air C=C stretching cyclic alkene out of plane C-H bending Absorbance (a.u.) Increasing temperature TMP Wavenumbers (cm -1 ) 19 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
20 TMP + HSAG 1/1 - from 25 to 150 C +HSAG Δ Air C=C stretching cyclic alkene Oxidation out of plane C-H bending Absorbance (a.u.) TMP+HSAG 1/1 130 C TMP+HSAG 1/1 100 C TMP+HSAG 1/1 80 C Increasing temperature TMP Wavenumbers (cm -1 ) 20 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
21 TMP + HSAG 1/1 - from 25 to 150 C +HSAG Δ Air C=C stretching cyclic alkene Oxidation out of plane C-H bending Absorbance (a.u.) TMP+HSAG 1/1 150 C TMP+HSAG 1/1 130 C TMP+HSAG 1/1 100 C TMP+HSAG 1/1 80 C Increasing temperature TMP Wavenumbers (cm -1 ) 21 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
22 Mechanistic path Paal-Knorr reaction HSAG 1 Paal Knorr Reaction 22 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
23 Mechanistic path Carbocatalyzed benzyl oxidation HSAG 1 2 Paal Knorr Reaction Carbocatalyzed Oxidation 23 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
24 Mechanistic path Increasing temperature * Structure confirmed by means of NMR spectroscopy 24 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
25 Mechanistic path Increasing temperature * Structure confirmed by means of NMR spectroscopy 25 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
26 Mechanistic path Increasing temperature 26 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
27 Model reaction and DFT calculation OHC * Structure confirmed by means of FT-IR and NMR spectroscopy 27 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017 DFT (B3LYP/ G(d,p))
28 Model reaction and DFT calculation OHC Abs TMP + Anthracene 150 C * Abs TMP + HSAG 130 C * Abs Abs Wavenumbers (cm -1 ) * Structure confirmed by means of FT-IR and NMR spectroscopy 28 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
29 Model reaction and DFT calculation OHC Abs TMP + Anthracene 150 C * Abs TMP + HSAG 130 C * Abs Abs Wavenumbers (cm -1 ) DFT (B3LYP/ G(d,p)) 29 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
30 Facile functionalization of carbon materials Hypothesis for the mechanism Carbon allotrope Paal Knorr Reaction Carbocatalyzed Oxidation Diels-Alder reaction 30 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
31 Facile functionalization of carbon materials Functional group: from few % to 20% Functionalization yield: from 85% to quantitative Covalent bond between functional group and graphene layer Bulk structure of graphitic materials: substantially unaltered V. Barbera, A. Citterio, M. Galimberti, G. Leonardi, R. Sebastiano, S.U. Shisodia, A.M. Valerio. WO/2015/ A1 (2015) M. Galimberti, V. Barbera, R. Sebastiano, A. Citterio, G. Leonardi, A.M. Valerio. WO/2016/ A1 (2016) M. Galimberti, V. Barbera, R. Sebastiano, A. Truscello, A.M. Valerio. WO/2016/ A1 (2016) M. Galimberti, V. Barbera, Italian Patent (2016) M. Galimberti, V. Barbera, Italian Patent (2016) 31 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
32 Nano-carbon Up Polyol dispersions Latex Monolithic dispersions aerogel Versatile Technology Rubber nanocomposites Polyurethane Carbon papers Conductive ink Conductive coating 32 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
33 Acknowledgments Thanks for the Attention 33 V. Barbera Domino reaction for the controlled AICIng - Milano June, 2017
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