Skip to content
DraconiticResearch
Search Sources API
203,234 studies31 sourcesUpdated 3 min ago
Peer-reviewedCC BYAngewandte Chemie International Edition

A Chiral Saddle‐Shaped Nanographene With Two Heptagon‐Embedded [4]Helicenes

  • Felix Trautner1,2
  • Boris Borrisov1
  • Philipp Royla3
  • Hongqing Zhao4
  • Hartmut Komber5
  • Li Wan2
  • Evgenia Dmitrieva6
  • Ji Ma7
  • Jan J. Weigand3
  • Qun Yang2
  • Xinliang Feng1,2
  • Wenhui Niu1,2
7 affiliations
  1. 1Center for Advancing Electronics Dresden (CFAED) & Faculty of Chemistry and Food Chemistry TECHNISCHE Universität Dresden Dresden Germany
  2. 2Max Planck Institute of Microstructure Physics Halle Germany
  3. 3Chair of Inorganic Molecular Chemistry Faculty of Chemistry and Food Chemistry Technische Universität Dresden Dresden Germany
  4. 4Faculty of Chemistry and Pharmacy Ludwig‐Maximilian‐Universität München Munich Germany
  5. 5Leibniz‐Institut Für Polymerforschung Dresden e. V. Dresden Germany
  6. 6Leibniz Institute for Solid State and Materials Research (IFW) Dresden Dresden Germany
  7. 7College of Materials Science and Optoelectronic Technology & Center of Materials Science and Optoelectronics Engineering University of Chinese Academy of Science Beijing China
Open at sourceDOICite

Abstract

Chiral non‐benzenoid nanographenes (NGs) remain highly appealing, yet underexplored synthetic targets due to the lack of feasible synthetic strategies to simultaneously construct non‐hexagonal rings and stable chirality. Herein, we demonstrate a novel synthetic strategy to construct a chiral saddle‐shaped nanographene ( cSNG ) via stepwise oxidation of an anthracene‐containing oligophenylene precursor. Scholl‐type oxidation first yields a key intermediate featuring sp 3 ‐defect heptagons, and subsequent oxidative dehydrogenation furnishes target cSNG incorporating two heptagon‐embedded [4]helicenes. The structure of cSNG is unambiguously confirmed by single‐crystal analysis, demonstrating its saddle‐shaped geometry with intrinsic chirality. Remarkably, due to the heptagon‐embedded [4]helicene subunits, cSNG exists as configurationally stable enantiomers which enable chiral resolution, leading to pronounced chiroptical responses and enhanced dissymmetry factors, compared with its sp 3 ‐defect precursor. Moreover, profiting from chiral saddle geometry with shape‐adaptive character, cSNG presents strong host–guest interactions with fullerenes, with association constants up to 2.3 × 10 4 M −1 for C 60 and 8.7 × 10 4 M −1 for C 70 , which are among the highest values reported for negatively curved nanographenes. Crystallographic analysis of cocrystals of cSNG with C 60 further revealed a distinct 1:3 binding mode for supramolecular complexation, featuring two fullerenes accommodated within the saddle cavity and two additional fullerenes externally shared between neighboring saddle units.

Related

  1. Exact benzannulation regulates packing and circularly polarized luminescence in a chiral bilayer nanographene
    Dan-Yang Wang, Nai-Te Yao, Zhi-Ao Li +4
    Chemical SciencePeer-reviewedCC BY-NC 3.0Full textOrganic chemistryPMC
  2. Photosensitive Phenothiazine-Fused [4]Helicenes
    Ling-Xiao Li, Gaoqiang Xu, Yue Zhang +5
    ChemRxivPreprintCC BYFull textOrganic chemistryChemRxiv
  3. Thermally activated delayed fluorescence in neutral and cationic stages of aza-nanographene decorated with 6.6.6 defects.
    Rohith Valavil Suku, Illia E Serdiuk, Krzysztof Dzieszkowski +5
    Chemical sciencePeer-reviewedCC BYFull textOrganic chemistryEurope PMC
  4. Simulated transient absorption reveals torsion-dependent nonradiative relaxation in a near-infrared nanographene emitter
    Royle Perez-Castillo, Victor M. Freixas, Hassiel Negrin-Yuvero +5
    Chemical SciencePeer-reviewedCC BY-NC 3.0Full textPhysical chemistryPMC
  5. Embedded Morgan Fingerprints for more efficient molecular property predictions with machine learning
    Emilio Nuñez-Andrade, Isaac Vidal-Daza, Rafael Gomez-Bombarelli +2
    ChemRxivPreprintLicence not statedGeneral chemistryChemRxiv

Cite

BibTeXRIS
BibTeX
@article{trautner2026chiral,
  title = {{A Chiral Saddle‐Shaped Nanographene With Two Heptagon‐Embedded [4]Helicenes}},
  author = {Felix Trautner and Boris Borrisov and Philipp Royla and Hongqing Zhao and Hartmut Komber and Li Wan and Evgenia Dmitrieva and Ji Ma and Jan J. Weigand and Qun Yang and Xinliang Feng and Wenhui Niu},
  journal = {Angewandte Chemie International Edition},
  year = {2026},
  month = jun,
  doi = {10.1002/anie.3481279},
  url = {https://doi.org/10.1002/anie.3481279},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - A Chiral Saddle‐Shaped Nanographene With Two Heptagon‐Embedded [4]Helicenes
AU  - Felix Trautner
AU  - Boris Borrisov
AU  - Philipp Royla
AU  - Hongqing Zhao
AU  - Hartmut Komber
AU  - Li Wan
AU  - Evgenia Dmitrieva
AU  - Ji Ma
AU  - Jan J. Weigand
AU  - Qun Yang
AU  - Xinliang Feng
AU  - Wenhui Niu
PY  - 2026
DA  - 2026/06/02
JO  - Angewandte Chemie International Edition
DO  - 10.1002/anie.3481279
UR  - https://doi.org/10.1002/anie.3481279
AB  - Chiral non‐benzenoid nanographenes (NGs) remain highly appealing, yet underexplored synthetic targets due to the lack of feasible synthetic strategies to simultaneously construct non‐hexagonal rings and stable chirality. Herein, we demonstrate a novel synthetic strategy to construct a chiral saddle‐shaped nanographene ( cSNG ) via stepwise oxidation of an anthracene‐containing oligophenylene precursor. Scholl‐type oxidation first yields a key intermediate featuring sp 3 ‐defect heptagons, and subsequent oxidative dehydrogenation furnishes target cSNG incorporating two heptagon‐embedded [4]helicenes. The structure of cSNG is unambiguously confirmed by single‐crystal analysis, demonstrating its saddle‐shaped geometry with intrinsic chirality. Remarkably, due to the heptagon‐embedded [4]helicene subunits, cSNG exists as configurationally stable enantiomers which enable chiral resolution, leading to pronounced chiroptical responses and enhanced dissymmetry factors, compared with its sp 3 ‐defect precursor. Moreover, profiting from chiral saddle geometry with shape‐adaptive character, cSNG presents strong host–guest interactions with fullerenes, with association constants up to 2.3 × 10 4 M −1 for C 60 and 8.7 × 10 4 M −1 for C 70 , which are among the highest values reported for negatively curved nanographenes. Crystallographic analysis of cocrystals of cSNG with C 60 further revealed a distinct 1:3 binding mode for supramolecular complexation, featuring two fullerenes accommodated within the saddle cavity and two additional fullerenes externally shared between neighboring saddle units.
SN  - 1433-7851
SN  - 1521-3773
ER  -