E-resources
Peer reviewed
-
Liu, Tong‐Xin; Wang, Xin; Xia, Shilu; Chen, Muqing; Li, Mingjie; Yang, Panting; Ma, Nana; Hu, Ziqi; Yang, Shangfeng; Zhang, Guisheng; Wang, Guan‐Wu
Angewandte Chemie International Edition, November 13, 2023, Volume: 62, Issue: 46Journal Article
Herein, we report divergent additions of 2,2′‐diazidobiphenyls to C60 and Sc3N@Ih‐C80. In stark contrast to that of the previously reported bis‐azide additions, the unexpected cascade reaction leads to the dearomative formation of azafulleroids 2 fused with a 7‐6‐5‐membered ring system in the case of C60. In contrast, the corresponding reaction with Sc3N@Ih‐C80 switches to the C−H insertion pathway, thereby resulting in multiple isomers, including a carbazole‐derived 6,6‐azametallofulleroid 3 and a 5,6‐azametallofulleroid 4 and an unusual 1,2,3,6‐tetrahydropyrrolo3,2‐ccarbazole‐derived metallofullerene 5, whose molecular structures have been unambiguously determined by single‐crystal X‐ray diffraction analyses. Among them, the addition type of 5 is observed for the first time in all reported additions of azides to fullerenes. Furthermore, unexpected isomerizations from 3 to 5 and from 4 to 5 have been discovered, providing the first examples of the isomerization of an azafulleroid to a carbazole‐derived fullerene rather than an aziridinofullerene. In particular, the isomerism of the 5,6‐isomer 4 to the 5,6‐isomer 5 is unprecedented in fullerene chemistry, contradicting the present understanding that isomerization generally occurs between 5,6‐ and 6,6‐isomers. Control experiments have been carried out to rationalize the reaction mechanism. Furthermore, representative azafulleroids have been applied in organic solar cells, thereby resulting in improved power conversion efficiencies. Divergent reactivities of 2,2′‐diazidobiphenyls toward C60 and Sc3N@Ih‐C80 have been disclosed. In the case of C60, a dearomative cascade reaction results in the formation of azafulleroids fused with a 7‐6‐5‐membered ring system, whereas Sc3N@Ih‐C80 undergoes a C−H insertion pathway, with the generation of carbazole‐derived 6,6‐ and 5,6‐azametallofulleroids and an unusual 1,2,3,6‐tetrahydropyrrolo3,2‐ccarbazole‐derived metallofullerene.
Author
![loading ... loading ...](themes/default/img/ajax-loading.gif)
Shelf entry
Permalink
- URL:
Impact factor
Access to the JCR database is permitted only to users from Slovenia. Your current IP address is not on the list of IP addresses with access permission, and authentication with the relevant AAI accout is required.
Year | Impact factor | Edition | Category | Classification | ||||
---|---|---|---|---|---|---|---|---|
JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
Select the library membership card:
If the library membership card is not in the list,
add a new one.
DRS, in which the journal is indexed
Database name | Field | Year |
---|
Links to authors' personal bibliographies | Links to information on researchers in the SICRIS system |
---|
Source: Personal bibliographies
and: SICRIS
The material is available in full text. If you wish to order the material anyway, click the Continue button.