Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions
The efficient binding of dicarboxylates represents an important yet challenging issue in supramolecular chemistry. In this study, we designed functional ultracycles as hosts to accommodate large organic dicarboxylate anions. These ultracycles were synthesized via a one-pot strategy starting from mac...
Saved in:
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2025-05-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.21.72 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849696632366432256 |
|---|---|
| author | Wen-Hui Mi Teng-Yu Huang Xu-Dong Wang Yu-Fei Ao Qi-Qiang Wang De-Xian Wang |
| author_facet | Wen-Hui Mi Teng-Yu Huang Xu-Dong Wang Yu-Fei Ao Qi-Qiang Wang De-Xian Wang |
| author_sort | Wen-Hui Mi |
| collection | DOAJ |
| description | The efficient binding of dicarboxylates represents an important yet challenging issue in supramolecular chemistry. In this study, we designed functional ultracycles as hosts to accommodate large organic dicarboxylate anions. These ultracycles were synthesized via a one-pot strategy starting from macrocyclic precursors. Host–dicarboxylate binding was investigated using 1H NMR titrations, revealing that B4aH exhibits strong binding affinities toward a series of dicarboxylates, with association constants reaching up to 6896 M−1. The selectivity for heptanedioate (C72−) was attributed to cooperative hydrogen bonding, anion–π interactions, and a size-matching effect, as supported by DFT optimizations. |
| format | Article |
| id | doaj-art-1854b0eb16c4473eaafae70f6c7e6751 |
| institution | DOAJ |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-1854b0eb16c4473eaafae70f6c7e67512025-08-20T03:19:24ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-05-0121188488910.3762/bjoc.21.721860-5397-21-72Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactionsWen-Hui Mi0Teng-Yu Huang1Xu-Dong Wang2Yu-Fei Ao3Qi-Qiang Wang4De-Xian Wang5Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China The efficient binding of dicarboxylates represents an important yet challenging issue in supramolecular chemistry. In this study, we designed functional ultracycles as hosts to accommodate large organic dicarboxylate anions. These ultracycles were synthesized via a one-pot strategy starting from macrocyclic precursors. Host–dicarboxylate binding was investigated using 1H NMR titrations, revealing that B4aH exhibits strong binding affinities toward a series of dicarboxylates, with association constants reaching up to 6896 M−1. The selectivity for heptanedioate (C72−) was attributed to cooperative hydrogen bonding, anion–π interactions, and a size-matching effect, as supported by DFT optimizations.https://doi.org/10.3762/bjoc.21.72anion–π interactionsanion recognitionhydrogen bondingdicarboxylatesultracycles |
| spellingShingle | Wen-Hui Mi Teng-Yu Huang Xu-Dong Wang Yu-Fei Ao Qi-Qiang Wang De-Xian Wang Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions Beilstein Journal of Organic Chemistry anion–π interactions anion recognition hydrogen bonding dicarboxylates ultracycles |
| title | Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions |
| title_full | Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions |
| title_fullStr | Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions |
| title_full_unstemmed | Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions |
| title_short | Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions |
| title_sort | dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion π interactions |
| topic | anion–π interactions anion recognition hydrogen bonding dicarboxylates ultracycles |
| url | https://doi.org/10.3762/bjoc.21.72 |
| work_keys_str_mv | AT wenhuimi dicarboxylaterecognitionbasedonultracyclehoststhroughcooperativehydrogenbondingandanionpinteractions AT tengyuhuang dicarboxylaterecognitionbasedonultracyclehoststhroughcooperativehydrogenbondingandanionpinteractions AT xudongwang dicarboxylaterecognitionbasedonultracyclehoststhroughcooperativehydrogenbondingandanionpinteractions AT yufeiao dicarboxylaterecognitionbasedonultracyclehoststhroughcooperativehydrogenbondingandanionpinteractions AT qiqiangwang dicarboxylaterecognitionbasedonultracyclehoststhroughcooperativehydrogenbondingandanionpinteractions AT dexianwang dicarboxylaterecognitionbasedonultracyclehoststhroughcooperativehydrogenbondingandanionpinteractions |