Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60
The “one-pot” synthesis of several homochiral macrocycles has been achieved by using π-electron-rich, electron-deficient or extended aromatic dicarboxylic acids in combination with an axially-chiral dibenzylic alcohol, derived from enantiomerically-pure BINOL. Two series of cyclic adducts with avera...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.132 |
| _version_ | 1818865752916099072 |
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| author | Marco Caricato Silvia Díez González Idoia Arandia Ariño Dario Pasini |
| author_facet | Marco Caricato Silvia Díez González Idoia Arandia Ariño Dario Pasini |
| author_sort | Marco Caricato |
| collection | DOAJ |
| description | The “one-pot” synthesis of several homochiral macrocycles has been achieved by using π-electron-rich, electron-deficient or extended aromatic dicarboxylic acids in combination with an axially-chiral dibenzylic alcohol, derived from enantiomerically-pure BINOL. Two series of cyclic adducts with average molecular D2 and D3 molecular symmetries, respectively, have been isolated in pure forms. Their yields and selectivities deviate substantially from statistical distributions. NMR and CD spectroscopic methods are efficient and functional in order to highlight the variability of shapes of the covalent macrocyclic frameworks. The larger D3 cyclic adducts exhibit recognition properties towards C60 in toluene solutions (up to log Ka = 3.2) with variable stoichiometries and variable intensities of the charge-tranfer band upon complexation. |
| first_indexed | 2024-12-19T10:52:33Z |
| format | Article |
| id | doaj.art-f0fb4e2d72d3450a921ccbddb3a81117 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T10:52:33Z |
| publishDate | 2014-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-f0fb4e2d72d3450a921ccbddb3a811172022-12-21T20:24:57ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-06-011011308131610.3762/bjoc.10.1321860-5397-10-132Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60Marco Caricato0Silvia Díez González1Idoia Arandia Ariño2Dario Pasini3Department of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, ItalyDepartment of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, ItalyDepartment of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, ItalyDepartment of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, ItalyThe “one-pot” synthesis of several homochiral macrocycles has been achieved by using π-electron-rich, electron-deficient or extended aromatic dicarboxylic acids in combination with an axially-chiral dibenzylic alcohol, derived from enantiomerically-pure BINOL. Two series of cyclic adducts with average molecular D2 and D3 molecular symmetries, respectively, have been isolated in pure forms. Their yields and selectivities deviate substantially from statistical distributions. NMR and CD spectroscopic methods are efficient and functional in order to highlight the variability of shapes of the covalent macrocyclic frameworks. The larger D3 cyclic adducts exhibit recognition properties towards C60 in toluene solutions (up to log Ka = 3.2) with variable stoichiometries and variable intensities of the charge-tranfer band upon complexation.https://doi.org/10.3762/bjoc.10.132BINOLC60carbon nanomaterialscarbon nanostructureschiralitymacrocyclessensorssupramolecular chemistry |
| spellingShingle | Marco Caricato Silvia Díez González Idoia Arandia Ariño Dario Pasini Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60 Beilstein Journal of Organic Chemistry BINOL C60 carbon nanomaterials carbon nanostructures chirality macrocycles sensors supramolecular chemistry |
| title | Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60 |
| title_full | Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60 |
| title_fullStr | Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60 |
| title_full_unstemmed | Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60 |
| title_short | Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C60 |
| title_sort | homochiral binol based macrocycles with π electron rich electron withdrawing or extended spacing units as receptors for c60 |
| topic | BINOL C60 carbon nanomaterials carbon nanostructures chirality macrocycles sensors supramolecular chemistry |
| url | https://doi.org/10.3762/bjoc.10.132 |
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