Synthesis of π-Conjugated Chiral Aza/Boracyclophanes with a meta and para Substitution
© 2023 Wiley-VCH GmbH..
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 |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:30 |
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| Enthalten in: |
Chemistry (Weinheim an der Bergstrasse, Germany) - 30(2024), 5 vom: 22. Jan., Seite e202302950 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhang, Kai [VerfasserIn] |
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| Links: |
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| Themen: |
π-Conjugated Macrocycles |
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| Anmerkungen: |
Date Revised 23.01.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/chem.202302950 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a © 2023 Wiley-VCH GmbH. | ||
| 520 | |a 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 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Axial Chirality | |
| 650 | 4 | |a Circularly Polarized Luminescence | |
| 650 | 4 | |a Organoborane | |
| 650 | 4 | |a Triarylamine | |
| 650 | 4 | |a π-Conjugated Macrocycles | |
| 700 | 1 | |a Hao, Mengyao |e verfasserin |4 aut | |
| 700 | 1 | |a Jin, Tianyun |e verfasserin |4 aut | |
| 700 | 1 | |a Shi, Yafei |e verfasserin |4 aut | |
| 700 | 1 | |a Tian, Guoqing |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Chenglong |e verfasserin |4 aut | |
| 700 | 1 | |a Ma, Hongwei |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Niu |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Quansong |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Pangkuan |e verfasserin |4 aut | |
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