Chiral Carbon Nanorings : Synthesis, Properties and Hierarchical Self-assembly of Chiral Ternary Complexes Featuring a Narcissistic Chiral Self-Recognition for Chiral Amines
© 2023 Wiley-VCH GmbH..
We report the synthesis and chiroptical properties of novel chiral carbon nanorings Sp-/Rp-[12]PCPP containing a planar chiral [2.2]PCP unit, and demonstrate that Sp-/Rp-[12]PCPP can not only host crown ether 18-Crown-6 to form ring-in-ring complexes with a binding constant 3.35×103 M-1 , but also accommodate the complexes of 18-Crown-6 and S/R-protonated amines to form homochiral SSp-/R@Rp- and heterochiral S@Rp-/R@Sp- ternary complexes, displaying significantly larger binding constants of up to 3.31×105 M-1 depending on the chiral guests. Importantly, homochiral S@Sp-/R@Rp- ternary complexes exhibit an enhanced CD signal, while the heterochiral S@Rp-/R@Sp- ones have a constant CD signal compared with the chiral carbon nanorings, respectively, which suggests that homochiral S@Sp-/R@Rp- ternary complexes display a highly narcissistic chiral self-recognition for S/R-protonated chiral amines, respectively. Finally, the chiral ternary complexes can be further applied to determine the ee values of chiral guests. The findings highlight a new application of carbon nanorings in supramolecular sensors, beyond the common recognition of π-conjugated molecules.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2023 |
|---|---|
| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:62 |
|---|---|
| Enthalten in: |
Angewandte Chemie (International ed. in English) - 62(2023), 28 vom: 10. Juli, Seite e202304623 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Fan, Yanqing [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
Chiral Amines |
|---|
| Anmerkungen: |
Date Completed 04.07.2023 Date Revised 04.07.2023 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
|---|
| doi: |
10.1002/anie.202304623 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM356965449 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM356965449 | ||
| 003 | DE-627 | ||
| 005 | 20231226071555.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231226s2023 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/anie.202304623 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1189.xml |
| 035 | |a (DE-627)NLM356965449 | ||
| 035 | |a (NLM)37193936 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Fan, Yanqing |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Chiral Carbon Nanorings |b Synthesis, Properties and Hierarchical Self-assembly of Chiral Ternary Complexes Featuring a Narcissistic Chiral Self-Recognition for Chiral Amines |
| 264 | 1 | |c 2023 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 04.07.2023 | ||
| 500 | |a Date Revised 04.07.2023 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2023 Wiley-VCH GmbH. | ||
| 520 | |a We report the synthesis and chiroptical properties of novel chiral carbon nanorings Sp-/Rp-[12]PCPP containing a planar chiral [2.2]PCP unit, and demonstrate that Sp-/Rp-[12]PCPP can not only host crown ether 18-Crown-6 to form ring-in-ring complexes with a binding constant 3.35×103 M-1 , but also accommodate the complexes of 18-Crown-6 and S/R-protonated amines to form homochiral SSp-/R@Rp- and heterochiral S@Rp-/R@Sp- ternary complexes, displaying significantly larger binding constants of up to 3.31×105 M-1 depending on the chiral guests. Importantly, homochiral S@Sp-/R@Rp- ternary complexes exhibit an enhanced CD signal, while the heterochiral S@Rp-/R@Sp- ones have a constant CD signal compared with the chiral carbon nanorings, respectively, which suggests that homochiral S@Sp-/R@Rp- ternary complexes display a highly narcissistic chiral self-recognition for S/R-protonated chiral amines, respectively. Finally, the chiral ternary complexes can be further applied to determine the ee values of chiral guests. The findings highlight a new application of carbon nanorings in supramolecular sensors, beyond the common recognition of π-conjugated molecules | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Chiral Amines | |
| 650 | 4 | |a Chiral Carbon Nanoring | |
| 650 | 4 | |a Chiral Self-recognition | |
| 650 | 4 | |a Chiral Ternary Complexes | |
| 650 | 4 | |a Narcissistic Recognition | |
| 700 | 1 | |a He, Jing |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Lin |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Guoqin |e verfasserin |4 aut | |
| 700 | 1 | |a Guo, Shengzhu |e verfasserin |4 aut | |
| 700 | 1 | |a Lian, Zhe |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Xiaonan |e verfasserin |4 aut | |
| 700 | 1 | |a Guo, Weijie |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Xuebo |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Ying |e verfasserin |4 aut | |
| 700 | 1 | |a Jiang, Hua |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Angewandte Chemie (International ed. in English) |d 1964 |g 62(2023), 28 vom: 10. Juli, Seite e202304623 |w (DE-627)NLM000105422 |x 1521-3773 |7 nnns |
| 773 | 1 | 8 | |g volume:62 |g year:2023 |g number:28 |g day:10 |g month:07 |g pages:e202304623 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1002/anie.202304623 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 62 |j 2023 |e 28 |b 10 |c 07 |h e202304623 | ||