Synthesis of Mono-, Di-, Tri-, and Tetra-cationic Pyridinium and Vinylpyridinium Modified [2.2]Paracyclophanes : Modular Receptors for Supramolecular Systems
© 2024 The Authors. ChemistryOpen published by Wiley-VCH GmbH..
In this report, a new series of mono-, di-, tri-, and tetra-cationic pyridinium and vinyl pyridinium-modified [2.2]paracyclophanes as useful molecular tectons for supramolecular systems are described. Regioselective functionalization at specific positions, followed by resolution step and successive transformations through Pd-catalyzed Suzuki-Miyaura and Mizoroki-Heck cross-coupling chemistry furnish a series of modular PCP scaffolds. In our proof-of-concept study, on N-methylation, the PCPs bearing (cationic) pyridyl functionalities were demonstrated as useful molecular receptors in host-guest supramolecular assays. The PCPs on grafting with light-responsive azobenzene (-N=N-) functional core as side-groups impart photosensitivity that can be remotely transformed on irradiation, offering photo-controlled smart molecular functions. Furthermore, the symmetrical PCPs bearing bi-, and tetra-pyridyl functionalities at the peripheries have enormous potential to serve as ditopic and tetratopic 3D molecular tectons for engineering non-covalent supramolecular assemblies with new structural and functional attributes.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - year:2024 |
|---|---|
| Enthalten in: |
ChemistryOpen - (2024) vom: 12. März, Seite e202400024 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Wang, Yichuan [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
[2.2]Paracyclophane |
|---|
| Anmerkungen: |
Date Revised 12.03.2024 published: Print-Electronic Citation Status Publisher |
|---|
| doi: |
10.1002/open.202400024 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM369616863 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM369616863 | ||
| 003 | DE-627 | ||
| 005 | 20240313235202.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 240313s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/open.202400024 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1326.xml |
| 035 | |a (DE-627)NLM369616863 | ||
| 035 | |a (NLM)38471964 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Wang, Yichuan |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis of Mono-, Di-, Tri-, and Tetra-cationic Pyridinium and Vinylpyridinium Modified [2.2]Paracyclophanes |b Modular Receptors for Supramolecular Systems |
| 264 | 1 | |c 2024 | |
| 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 Revised 12.03.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status Publisher | ||
| 520 | |a © 2024 The Authors. ChemistryOpen published by Wiley-VCH GmbH. | ||
| 520 | |a In this report, a new series of mono-, di-, tri-, and tetra-cationic pyridinium and vinyl pyridinium-modified [2.2]paracyclophanes as useful molecular tectons for supramolecular systems are described. Regioselective functionalization at specific positions, followed by resolution step and successive transformations through Pd-catalyzed Suzuki-Miyaura and Mizoroki-Heck cross-coupling chemistry furnish a series of modular PCP scaffolds. In our proof-of-concept study, on N-methylation, the PCPs bearing (cationic) pyridyl functionalities were demonstrated as useful molecular receptors in host-guest supramolecular assays. The PCPs on grafting with light-responsive azobenzene (-N=N-) functional core as side-groups impart photosensitivity that can be remotely transformed on irradiation, offering photo-controlled smart molecular functions. Furthermore, the symmetrical PCPs bearing bi-, and tetra-pyridyl functionalities at the peripheries have enormous potential to serve as ditopic and tetratopic 3D molecular tectons for engineering non-covalent supramolecular assemblies with new structural and functional attributes | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a 3D Molecular Tectons | |
| 650 | 4 | |a Cationic Pyridines | |
| 650 | 4 | |a Cross-coupling chemistry | |
| 650 | 4 | |a Molecular receptors | |
| 650 | 4 | |a Supramolecular Interactions | |
| 650 | 4 | |a [2.2]Paracyclophane | |
| 700 | 1 | |a Li, Yuting |e verfasserin |4 aut | |
| 700 | 1 | |a Fuhr, Olaf |e verfasserin |4 aut | |
| 700 | 1 | |a Nieger, Martin |e verfasserin |4 aut | |
| 700 | 1 | |a Hassan, Zahid |e verfasserin |4 aut | |
| 700 | 1 | |a Bräse, Stefan |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t ChemistryOpen |d 2012 |g (2024) vom: 12. März, Seite e202400024 |w (DE-627)NLM230518664 |x 2191-1363 |7 nnns |
| 773 | 1 | 8 | |g year:2024 |g day:12 |g month:03 |g pages:e202400024 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1002/open.202400024 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |j 2024 |b 12 |c 03 |h e202400024 | ||