Synthesis of π‐Conjugated Chiral Aza/Boracyclophanes with a meta and para Substitution
Abstract We herein describe the synthesis of a new class of axially chiral aza/boracyclophanes ( BDN1, BXN1, BDB1 and BXB1) using binaphthyls as chiral building blocks and the main‐group (B/N) chemistry with tunable electronic effects. All macrocycles substituted with triarylamine donors or triarylborane acceptors are strongly luminescent. These macrocycles showed two distinct meta and para π‐conjugation pathways, leading to the formation of quasi figure‐of‐eight and square‐shaped conformations. Interestingly, comparison of such structural models revealed that the former type of macrocycles BXN1 and BXB1 gave higher racemization barriers relative to the other ones. The results reported here may provide a new approach to engineer the optical stability of π‐conjugated chiral macrocycles by controlling π‐substitution patterns. The ring constraints induced by macrocyclization were also demonstrated to contribute to the configurational persistence as compared with the open‐chain analogues p‐BTT and m‐BTT..
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:30 |
|---|---|
| Enthalten in: |
Chemistry – A European Journal - 30(2024), 5 |
| Beteiligte Personen: |
Zhang, Kai [VerfasserIn] |
|---|
| Anmerkungen: |
© 2024 Wiley‐VCH GmbH |
|---|
| Umfang: |
8 |
|---|
| doi: |
10.1002/chem.202302950 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
WLY017378206 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | WLY017378206 | ||
| 003 | DE-627 | ||
| 005 | 20240422171747.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 240422s2024 xx |||||o 00| ||und c | ||
| 024 | 7 | |a 10.1002/chem.202302950 |2 doi | |
| 028 | 5 | 2 | |a 2024-04-22_CHEM_2024_30_5.zip.xml |
| 035 | |a (DE-627)WLY017378206 | ||
| 035 | |a (WILEY)CHEM202302950 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 100 | 1 | |a Zhang, Kai |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis of π‐Conjugated Chiral Aza/Boracyclophanes with a meta and para Substitution |
| 264 | 1 | |c 2024 | |
| 300 | |a 8 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a © 2024 Wiley‐VCH GmbH | ||
| 520 | |a Abstract We herein describe the synthesis of a new class of axially chiral aza/boracyclophanes ( BDN1, BXN1, BDB1 and BXB1) using binaphthyls as chiral building blocks and the main‐group (B/N) chemistry with tunable electronic effects. All macrocycles substituted with triarylamine donors or triarylborane acceptors are strongly luminescent. These macrocycles showed two distinct meta and para π‐conjugation pathways, leading to the formation of quasi figure‐of‐eight and square‐shaped conformations. Interestingly, comparison of such structural models revealed that the former type of macrocycles BXN1 and BXB1 gave higher racemization barriers relative to the other ones. The results reported here may provide a new approach to engineer the optical stability of π‐conjugated chiral macrocycles by controlling π‐substitution patterns. The ring constraints induced by macrocyclization were also demonstrated to contribute to the configurational persistence as compared with the open‐chain analogues p‐BTT and m‐BTT. | ||
| 700 | 1 | |a Hao, Mengyao |4 aut | |
| 700 | 1 | |a Jin, Tianyun |4 aut | |
| 700 | 1 | |a Shi, Yafei |4 aut | |
| 700 | 1 | |a Tian, Guoqing |4 aut | |
| 700 | 1 | |a Li, Chenglong |4 aut | |
| 700 | 1 | |a Ma, Hongwei |4 aut | |
| 700 | 1 | |a Zhang, Niu |4 aut | |
| 700 | 1 | |a Li, Quansong |4 aut | |
| 700 | 1 | |a Chen, Pangkuan |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Chemistry – A European Journal |g 30(2024), 5 |w (DE-627)WLY003422275 |x 15213765 |7 nnns |
| 773 | 1 | 8 | |g volume:30 |g year:2024 |g number:5 |g extent:8 |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_WLY | ||
| 951 | |a AR | ||
| 952 | |d 30 |j 2024 |e 5 |g 8 | ||