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Peer-reviewedCC BY-NC 3.0Chemical Science

Exact benzannulation regulates packing and circularly polarized luminescence in a chiral bilayer nanographene

  • Dan-Yang Wang1
  • Nai-Te Yao1
  • Zhi-Ao Li1
  • Jiaqi Liang1,2
  • Ke-Lin Zhu1
  • Bin Hu1
  • Han-Yuan Gong1
  1. 1College of Chemistry, Beijing Normal University No. 19, XinWai St, HaiDian District Beijing 100875 China
  2. 2School of Chemistry & Environment, Yunnan Minzu University No. 2929, Yuehua St, Chenggong District Kunming 650500 Yunnan Province China
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Abstract

Exact π-extension offers a molecularly precise approach for interrogating how peripheral structural modification governs the conformation, packing, and chiroptical response of atomically defined chiral nanographenes. Here we report DN-1, a naphthalene-extended chiral bilayer nanographene that reveals the regulatory role of peripheral benzannulation in supramolecular organization and circularly polarized luminescence. DN-1 was obtained by Scholl cyclodehydrogenation, forming 27 C–C bonds in a single operation. Single-crystal X-ray diffraction established a C2 symmetric bilayer architecture bearing peripheral naphthalene units and a short intramolecular interlayer separation of 2.945 Å. Notably, benzannulation does more than expand the π-surface: it reorganizes the solid-state packing and enables extensive intermolecular π-overlap involving up to 32 benzene rings. NMR spectroscopy and HRMS analyses verified the molecular identity, while NICS, AICD, and TD-DFT calculations clarified the aromaticity distribution and excited-state electronic structure. After chiral resolution, DN-1 displayed broad visible absorption, red emission at 677 nm, mirror-image circular dichroism, and circularly polarized luminescence at ca. 682 nm with |glum| values up to 1.79 × 10−2. These results establish exact benzannulation as a molecular design principle for linking peripheral π-extension, supramolecular packing, and CPL activity in chiral nanographenes.

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Cite

BibTeXRIS
BibTeX
@article{wang2026exact,
  title = {{Exact benzannulation regulates packing and circularly polarized luminescence in a chiral bilayer nanographene}},
  author = {Dan-Yang Wang and Nai-Te Yao and Zhi-Ao Li and Jiaqi Liang and Ke-Lin Zhu and Bin Hu and Han-Yuan Gong},
  journal = {Chemical Science},
  year = {2026},
  month = sep,
  doi = {10.1039/d6sc06566j},
  url = {https://doi.org/10.1039/d6sc06566j},
  note = {CC BY-NC 3.0},
}
RIS
TY  - JOUR
TI  - Exact benzannulation regulates packing and circularly polarized luminescence in a chiral bilayer nanographene
AU  - Dan-Yang Wang
AU  - Nai-Te Yao
AU  - Zhi-Ao Li
AU  - Jiaqi Liang
AU  - Ke-Lin Zhu
AU  - Bin Hu
AU  - Han-Yuan Gong
PY  - 2026
DA  - 2026/09/14
JO  - Chemical Science
DO  - 10.1039/d6sc06566j
UR  - https://doi.org/10.1039/d6sc06566j
AB  - Exact π-extension offers a molecularly precise approach for interrogating how peripheral structural modification governs the conformation, packing, and chiroptical response of atomically defined chiral nanographenes. Here we report DN-1, a naphthalene-extended chiral bilayer nanographene that reveals the regulatory role of peripheral benzannulation in supramolecular organization and circularly polarized luminescence. DN-1 was obtained by Scholl cyclodehydrogenation, forming 27 C–C bonds in a single operation. Single-crystal X-ray diffraction established a C2 symmetric bilayer architecture bearing peripheral naphthalene units and a short intramolecular interlayer separation of 2.945 Å. Notably, benzannulation does more than expand the π-surface: it reorganizes the solid-state packing and enables extensive intermolecular π-overlap involving up to 32 benzene rings. NMR spectroscopy and HRMS analyses verified the molecular identity, while NICS, AICD, and TD-DFT calculations clarified the aromaticity distribution and excited-state electronic structure. After chiral resolution, DN-1 displayed broad visible absorption, red emission at 677 nm, mirror-image circular dichroism, and circularly polarized luminescence at ca. 682 nm with |glum| values up to 1.79 × 10−2. These results establish exact benzannulation as a molecular design principle for linking peripheral π-extension, supramolecular packing, and CPL activity in chiral nanographenes.
SN  - 2041-6520
SN  - 2041-6539
ER  -