β-D-Galactose-Functionalized Pillar[5]arene With Interesting Planar-Chirality for Constructing Chiral Nanoparticles
Planar-chiral pillar[5]arenes bearing β-D-galactose substituents on both rims have been successfully synthesized and effectively separated by silica gel chromatography with a high yield. The obtained (Sp)- and (Rp)-β-D-galactose functionalized pillar[5]arenes [(Sp-D)-GP5 and (Rp-D)-GP5] exhibit the...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Frontiers Media S.A.
2019-11-01
|
| Series: | Frontiers in Chemistry |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2019.00743/full |
| _version_ | 1819179558288490496 |
|---|---|
| author | Guangping Sun Liangtao Pu Srikala Pangannaya Tangxin Xiao Xiao-Yu Hu Xiao-Yu Hu Juli Jiang Leyong Wang Leyong Wang |
| author_facet | Guangping Sun Liangtao Pu Srikala Pangannaya Tangxin Xiao Xiao-Yu Hu Xiao-Yu Hu Juli Jiang Leyong Wang Leyong Wang |
| author_sort | Guangping Sun |
| collection | DOAJ |
| description | Planar-chiral pillar[5]arenes bearing β-D-galactose substituents on both rims have been successfully synthesized and effectively separated by silica gel chromatography with a high yield. The obtained (Sp)- and (Rp)-β-D-galactose functionalized pillar[5]arenes [(Sp-D)-GP5 and (Rp-D)-GP5] exhibit the Sp and Rp planar chirality. Furthermore, (Sp-D)-GP5 and (Rp-D)-GP5 can not racemize according to dynamic 1H NMR and CD spectra. Notably, GP5 is able to capture a guest molecule (DNS-CPT) to form a host-guest supramolecular amphiphile, which can further self-assemble into chiral nanoparticles with the Sp and Rp planar chirality of (Sp-D)-GP5 and (Rp-D)-GP5 still being retained, suggesting GP5 could be as reliable chiral sources to transfer the Sp and Rp planar chirality. |
| first_indexed | 2024-12-22T22:00:21Z |
| format | Article |
| id | doaj.art-de8ee22056234cf1b873f8e2446a4fbb |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-22T22:00:21Z |
| publishDate | 2019-11-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-de8ee22056234cf1b873f8e2446a4fbb2022-12-21T18:11:09ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462019-11-01710.3389/fchem.2019.00743494724β-D-Galactose-Functionalized Pillar[5]arene With Interesting Planar-Chirality for Constructing Chiral NanoparticlesGuangping Sun0Liangtao Pu1Srikala Pangannaya2Tangxin Xiao3Xiao-Yu Hu4Xiao-Yu Hu5Juli Jiang6Leyong Wang7Leyong Wang8Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, ChinaState Key Laboratory of Pollution Control and Resource Reuse, School of Environment, Nanjing University, Nanjing, ChinaKey Laboratory of Mesoscopic Chemistry of Ministry of Education, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, ChinaSchool of Petrochemical Engineering, Changzhou University, Changzhou, ChinaKey Laboratory of Mesoscopic Chemistry of Ministry of Education, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, ChinaCollege of Material Science and Technology, Nanjing University of Aeronautics and Astronautics, Nanjing, ChinaKey Laboratory of Mesoscopic Chemistry of Ministry of Education, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, ChinaKey Laboratory of Mesoscopic Chemistry of Ministry of Education, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, ChinaSchool of Petrochemical Engineering, Changzhou University, Changzhou, ChinaPlanar-chiral pillar[5]arenes bearing β-D-galactose substituents on both rims have been successfully synthesized and effectively separated by silica gel chromatography with a high yield. The obtained (Sp)- and (Rp)-β-D-galactose functionalized pillar[5]arenes [(Sp-D)-GP5 and (Rp-D)-GP5] exhibit the Sp and Rp planar chirality. Furthermore, (Sp-D)-GP5 and (Rp-D)-GP5 can not racemize according to dynamic 1H NMR and CD spectra. Notably, GP5 is able to capture a guest molecule (DNS-CPT) to form a host-guest supramolecular amphiphile, which can further self-assemble into chiral nanoparticles with the Sp and Rp planar chirality of (Sp-D)-GP5 and (Rp-D)-GP5 still being retained, suggesting GP5 could be as reliable chiral sources to transfer the Sp and Rp planar chirality.https://www.frontiersin.org/article/10.3389/fchem.2019.00743/fullsupramolecular macrocyclesβ-D-galactose-functionalized pillar[5]arenesplanar chiralityself-assemblynanoparticles |
| spellingShingle | Guangping Sun Liangtao Pu Srikala Pangannaya Tangxin Xiao Xiao-Yu Hu Xiao-Yu Hu Juli Jiang Leyong Wang Leyong Wang β-D-Galactose-Functionalized Pillar[5]arene With Interesting Planar-Chirality for Constructing Chiral Nanoparticles Frontiers in Chemistry supramolecular macrocycles β-D-galactose-functionalized pillar[5]arenes planar chirality self-assembly nanoparticles |
| title | β-D-Galactose-Functionalized Pillar[5]arene With Interesting Planar-Chirality for Constructing Chiral Nanoparticles |
| title_full | β-D-Galactose-Functionalized Pillar[5]arene With Interesting Planar-Chirality for Constructing Chiral Nanoparticles |
| title_fullStr | β-D-Galactose-Functionalized Pillar[5]arene With Interesting Planar-Chirality for Constructing Chiral Nanoparticles |
| title_full_unstemmed | β-D-Galactose-Functionalized Pillar[5]arene With Interesting Planar-Chirality for Constructing Chiral Nanoparticles |
| title_short | β-D-Galactose-Functionalized Pillar[5]arene With Interesting Planar-Chirality for Constructing Chiral Nanoparticles |
| title_sort | β d galactose functionalized pillar 5 arene with interesting planar chirality for constructing chiral nanoparticles |
| topic | supramolecular macrocycles β-D-galactose-functionalized pillar[5]arenes planar chirality self-assembly nanoparticles |
| url | https://www.frontiersin.org/article/10.3389/fchem.2019.00743/full |
| work_keys_str_mv | AT guangpingsun bdgalactosefunctionalizedpillar5arenewithinterestingplanarchiralityforconstructingchiralnanoparticles AT liangtaopu bdgalactosefunctionalizedpillar5arenewithinterestingplanarchiralityforconstructingchiralnanoparticles AT srikalapangannaya bdgalactosefunctionalizedpillar5arenewithinterestingplanarchiralityforconstructingchiralnanoparticles AT tangxinxiao bdgalactosefunctionalizedpillar5arenewithinterestingplanarchiralityforconstructingchiralnanoparticles AT xiaoyuhu bdgalactosefunctionalizedpillar5arenewithinterestingplanarchiralityforconstructingchiralnanoparticles AT xiaoyuhu bdgalactosefunctionalizedpillar5arenewithinterestingplanarchiralityforconstructingchiralnanoparticles AT julijiang bdgalactosefunctionalizedpillar5arenewithinterestingplanarchiralityforconstructingchiralnanoparticles AT leyongwang bdgalactosefunctionalizedpillar5arenewithinterestingplanarchiralityforconstructingchiralnanoparticles AT leyongwang bdgalactosefunctionalizedpillar5arenewithinterestingplanarchiralityforconstructingchiralnanoparticles |