Molecular Design, Precise Synthesis and Solution Self-assembly of Molecular Patchy Particles
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University of Akron / OhioLINK
2016
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ndltd-OhioLink-oai-etd.ohiolink.edu-akron14603248622021-08-03T06:35:32Z Molecular Design, Precise Synthesis and Solution Self-assembly of Molecular Patchy Particles Zhou, Yangbin Molecular Chemistry Patchy particles are particles with precisely controlled dual or multiple surfaces of varying properties. Over the past decade, tremendous attentions have been paid on patchy particles due to their unique properties, anisotropic interactions and intriguing self-assembling behaviors. In this work, three molecular patchy particles based on precisely functionalized fullerenes (C60) were synthesized. Two of them contain ten amino groups on the surface of C60 but with different “patches”, which are four hydroxyl groups (NC60-4OH) or two carboxylic acids groups (NC60-2COOH). Starting from C60, two mono-functionalized C60 derivatives containing two protected carboxylic acids (C60-2tBu) or four protected hydroxyl groups (C60-4pre-OH) were synthesized in the dilute solution of toluene under the typical condition of Bingel-Hirsch reactions. C60-2tBu and C60-4pre-OH were further functionalized with ten protected amino groups in concentrated solution of dichlrobenzene to give BNC60-4pre-OH and BNC60-2tBu with protected groups, respectively. The deprotection of BNC60-4pre-OH and BNC60-2tBu were achieved in the solution of trifluoroacetic acid/dichloromethane to afford the final products NC60-4OH and NC60-2COOH, respectively. Another patchy particle (AC60-2NH2), which contains ten carboxylic acid groups on the surface of C60 and two amino groups as a patch, was synthesized following the similar reaction. For these three patchy particles, the precisely defined structures of as-synthesized intermediates and final products were fully characterized by Matrix-assisted laser desorption/ionization-time-of-flight (MALDI-TOF) mass spectra and Nuclear Magnetic Resonance (NMR) Spectroscope, including 1H NMR and 13C NMR. The self-assembly behavior of these patchy particles were investigated in different polar solvent such as THF, H2O, DMF. It was found that AC60-2NH2 could form vesicles in THF and tubes in H2O. Finally, different from commonly reported colloid patchy particles, whose sizes are in micrometer scale, the molecular patchy particles we synthesized are in nanometer scale and might provide a new perspective for the nanostructure formation of patchy particles. 2016-06-13 English text University of Akron / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=akron1460324862 http://rave.ohiolink.edu/etdc/view?acc_num=akron1460324862 unrestricted This thesis or dissertation is protected by copyright: all rights reserved. It may not be copied or redistributed beyond the terms of applicable copyright laws. |
| collection |
NDLTD |
| language |
English |
| sources |
NDLTD |
| topic |
Molecular Chemistry |
| spellingShingle |
Molecular Chemistry Zhou, Yangbin Molecular Design, Precise Synthesis and Solution Self-assembly of Molecular Patchy Particles |
| author |
Zhou, Yangbin |
| author_facet |
Zhou, Yangbin |
| author_sort |
Zhou, Yangbin |
| title |
Molecular Design, Precise Synthesis and Solution Self-assembly of Molecular Patchy Particles |
| title_short |
Molecular Design, Precise Synthesis and Solution Self-assembly of Molecular Patchy Particles |
| title_full |
Molecular Design, Precise Synthesis and Solution Self-assembly of Molecular Patchy Particles |
| title_fullStr |
Molecular Design, Precise Synthesis and Solution Self-assembly of Molecular Patchy Particles |
| title_full_unstemmed |
Molecular Design, Precise Synthesis and Solution Self-assembly of Molecular Patchy Particles |
| title_sort |
molecular design, precise synthesis and solution self-assembly of molecular patchy particles |
| publisher |
University of Akron / OhioLINK |
| publishDate |
2016 |
| url |
http://rave.ohiolink.edu/etdc/view?acc_num=akron1460324862 |
| work_keys_str_mv |
AT zhouyangbin moleculardesignprecisesynthesisandsolutionselfassemblyofmolecularpatchyparticles |
| _version_ |
1719439450621083648 |