Enhanced mechanical and thermal strength in mixed enantiomers based supramolecular gel
Mixing supramolecular gels based on enantiomers leads to re-arrangement of gel fibers at the molecular level, which results in more favorable packing and tuneable properties. Bis(urea) compounds tagged with a phenylalanine methyl ester in racemic and enantiopure forms were syn-thesized. Both enantio...
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American Chemical Society
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Online Access: | http://hdl.handle.net/1822/56717 https://doi.org/10.1021/acs.langmuir.8b02729 |
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ftunivminho:oai:repositorium.sdum.uminho.pt:1822/56717 2023-05-15T16:47:45+02:00 Enhanced mechanical and thermal strength in mixed enantiomers based supramolecular gel Tómasson, Daníel Arnar Ghosh, Dipankar Krinik, Zala Fasolin, Luiz H. Vicente, A. A. Martin, Adam D. Thordarson, Pall Damodaran, Krishna Kumar 2018-10 application/pdf http://hdl.handle.net/1822/56717 https://doi.org/10.1021/acs.langmuir.8b02729 eng eng American Chemical Society info:eu-repo/grantAgreement/FCT/5876/147337/PT http://pubs.acs.org/journal/langd5 Tómasson, Daníel Arnar; Ghosh, Dipankar; Krinik, Zala; Fasolin, Luiz H.; Vicente, António A.; Martin, Adam D.; Thordarson, Pall; Damodaran, Krishna Kumar, Enhanced mechanical and thermal strength in mixed enantiomers based supramolecular gel. Langmuir, 34(43), 12957-12967, 2018 0743-7463 http://hdl.handle.net/1822/56717 1520-5827 doi:10.1021/acs.langmuir.8b02729 30272986 info:eu-repo/semantics/openAccess Science & Technology info:eu-repo/semantics/article 2018 ftunivminho https://doi.org/10.1021/acs.langmuir.8b02729 2022-03-20T08:12:29Z Mixing supramolecular gels based on enantiomers leads to re-arrangement of gel fibers at the molecular level, which results in more favorable packing and tuneable properties. Bis(urea) compounds tagged with a phenylalanine methyl ester in racemic and enantiopure forms were syn-thesized. Both enantiopure and racemate compounds formed gels in a wide range of solvents and the racemate (1-rac) formed a stronger gel network compared to the enantiomers. The gel (1R+1S) obtained by mixing equimolar amount of enantiomers (1R and 1S) showed enhanced mechanical and thermal stability compared to enantiomers and racemate gels. The preservation of chirality in these compounds was analyzed by circular dichroism and optical rotation measurements. Analysis of the SEM and AFM images revealed that the network in the mixed gel is a combination of enantiomers and racemate fibers, which was further supported by solid state NMR. The analysis of the packing in xerogels by solid state NMR spectra and the existence of twisted-tape morphology in SEM and AFM images confirmed the presence of both self-sorted and co-assembled fibers in mixed gel. The enhanced thermal and mechanical strength may be attributed to the enhanced intermolecular forces between the racemate and enantiomer and the combination of both self-sorted and co-assembled enantiomers in the mixed gel. We thank University of Iceland Research Fund for financial support. D.G. thanks University of Iceland for the Doctoral Research grant and Z.K. thanks University of Ljubljana for the Erasmus exchange program. We thankfully acknowledge Dr. A. Rawal, The Mark Wainwright Analytical Centre, UNSW for solid state NMR studies and Dr. Sigrídur Jónsdóttir, University of Iceland for solution NMR and Mass spectroscopy. P.T. thanks the Australian Research Council for an ARC Centre of Excellence grant (CE140100036) and A.D.M. thanks the National Health and Medical Research Council for a Dementia Development Research Fellowship (APP1106751). L.F. and A.V. thank the FCT ... Article in Journal/Newspaper Iceland Universidade of Minho: RepositóriUM Langmuir 34 43 12957 12967 |
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Science & Technology |
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Science & Technology Tómasson, Daníel Arnar Ghosh, Dipankar Krinik, Zala Fasolin, Luiz H. Vicente, A. A. Martin, Adam D. Thordarson, Pall Damodaran, Krishna Kumar Enhanced mechanical and thermal strength in mixed enantiomers based supramolecular gel |
topic_facet |
Science & Technology |
description |
Mixing supramolecular gels based on enantiomers leads to re-arrangement of gel fibers at the molecular level, which results in more favorable packing and tuneable properties. Bis(urea) compounds tagged with a phenylalanine methyl ester in racemic and enantiopure forms were syn-thesized. Both enantiopure and racemate compounds formed gels in a wide range of solvents and the racemate (1-rac) formed a stronger gel network compared to the enantiomers. The gel (1R+1S) obtained by mixing equimolar amount of enantiomers (1R and 1S) showed enhanced mechanical and thermal stability compared to enantiomers and racemate gels. The preservation of chirality in these compounds was analyzed by circular dichroism and optical rotation measurements. Analysis of the SEM and AFM images revealed that the network in the mixed gel is a combination of enantiomers and racemate fibers, which was further supported by solid state NMR. The analysis of the packing in xerogels by solid state NMR spectra and the existence of twisted-tape morphology in SEM and AFM images confirmed the presence of both self-sorted and co-assembled fibers in mixed gel. The enhanced thermal and mechanical strength may be attributed to the enhanced intermolecular forces between the racemate and enantiomer and the combination of both self-sorted and co-assembled enantiomers in the mixed gel. We thank University of Iceland Research Fund for financial support. D.G. thanks University of Iceland for the Doctoral Research grant and Z.K. thanks University of Ljubljana for the Erasmus exchange program. We thankfully acknowledge Dr. A. Rawal, The Mark Wainwright Analytical Centre, UNSW for solid state NMR studies and Dr. Sigrídur Jónsdóttir, University of Iceland for solution NMR and Mass spectroscopy. P.T. thanks the Australian Research Council for an ARC Centre of Excellence grant (CE140100036) and A.D.M. thanks the National Health and Medical Research Council for a Dementia Development Research Fellowship (APP1106751). L.F. and A.V. thank the FCT ... |
format |
Article in Journal/Newspaper |
author |
Tómasson, Daníel Arnar Ghosh, Dipankar Krinik, Zala Fasolin, Luiz H. Vicente, A. A. Martin, Adam D. Thordarson, Pall Damodaran, Krishna Kumar |
author_facet |
Tómasson, Daníel Arnar Ghosh, Dipankar Krinik, Zala Fasolin, Luiz H. Vicente, A. A. Martin, Adam D. Thordarson, Pall Damodaran, Krishna Kumar |
author_sort |
Tómasson, Daníel Arnar |
title |
Enhanced mechanical and thermal strength in mixed enantiomers based supramolecular gel |
title_short |
Enhanced mechanical and thermal strength in mixed enantiomers based supramolecular gel |
title_full |
Enhanced mechanical and thermal strength in mixed enantiomers based supramolecular gel |
title_fullStr |
Enhanced mechanical and thermal strength in mixed enantiomers based supramolecular gel |
title_full_unstemmed |
Enhanced mechanical and thermal strength in mixed enantiomers based supramolecular gel |
title_sort |
enhanced mechanical and thermal strength in mixed enantiomers based supramolecular gel |
publisher |
American Chemical Society |
publishDate |
2018 |
url |
http://hdl.handle.net/1822/56717 https://doi.org/10.1021/acs.langmuir.8b02729 |
genre |
Iceland |
genre_facet |
Iceland |
op_relation |
info:eu-repo/grantAgreement/FCT/5876/147337/PT http://pubs.acs.org/journal/langd5 Tómasson, Daníel Arnar; Ghosh, Dipankar; Krinik, Zala; Fasolin, Luiz H.; Vicente, António A.; Martin, Adam D.; Thordarson, Pall; Damodaran, Krishna Kumar, Enhanced mechanical and thermal strength in mixed enantiomers based supramolecular gel. Langmuir, 34(43), 12957-12967, 2018 0743-7463 http://hdl.handle.net/1822/56717 1520-5827 doi:10.1021/acs.langmuir.8b02729 30272986 |
op_rights |
info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.1021/acs.langmuir.8b02729 |
container_title |
Langmuir |
container_volume |
34 |
container_issue |
43 |
container_start_page |
12957 |
op_container_end_page |
12967 |
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1766037851549466624 |