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Peer-reviewedCC BYJournal of the American Chemical Society

On-Surface Synthesis of a Low Bandgap Cyclopenta[c,d]azulene-Based Polymer.

  • S Jiménez-Fernández1
  • F Villalobos2
  • V Kumar3
  • J I Martínez1
  • J I Mendieta-Moreno4
  • P L de Andrés1
  • E Tosi1
  • J A Martín-Gago1
  • J M Cuerva3
  • I Palacio1
  • A G Campaña3
  • C Sánchez-Sánchez1
4 affiliations
  1. 1ESISNA Group, Instituto de Ciencia de Materiales de Madrid (ICMM-CSIC), Sor Juana Inés de la Cruz 3, Madrid28049, Spain.
  2. 2Institute of Physics of the Czech Academy of Sciences, Cukrovarnická 112/10, Prague 6162 00, Czech Republic.
  3. 3Departamento de Química Orgánica, Universidad de Granada (UGR), Unidad de Excelencia de Química UEQ, C. U. Fuentenueva, Granada18071, Spain.
  4. 4Departamento de Física Teórica de la Materia Condensada, Universidad Autónoma de Madrid, Madrid28049, Spain.
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Abstract

Nonbenzenoid topologies offer a compelling strategy to tailor the electronic properties of low-dimensional carbon materials. Here, we report the on-surface synthesis of a nonalternant polymer incorporating a [7-5-5] cyclopenta[c,d]azulene (CPA) motif on Au(111) via thermally induced Ullmann coupling. Bond-resolved scanning tunneling microscopy confirms the robustness of the [7-5-5] framework. Scanning tunneling spectroscopy, together with dI/dV mapping supported by density functional theory calculations, reveals a remarkable narrow polymeric bandgap of 1.5 eV. The electronic structure is governed by the intramolecular charge transfer from the heptagonal ring to the adjacent fused pentagonal rings, resulting in a pronounced dipole moment despite being composed exclusively of carbon and hydrogen. Aromaticity analyses indicate the coexistence of locally aromatic and slightly antiaromatic regions, highlighting the intrinsic electronic frustration associated with the nonalternant topology. These findings demonstrate how the controlled incorporation of [7-5-5] motifs enables the rational bandgap engineering in carbon-based polymers and expands the scope of nonbenzenoid design in on-surface synthesis.

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Cite

BibTeXRIS
BibTeX
@article{jimenezfernandez2026onsurface,
  title = {{On-Surface Synthesis of a Low Bandgap Cyclopenta[c,d]azulene-Based Polymer.}},
  author = {S Jiménez-Fernández and F Villalobos and V Kumar and J I Martínez and J I Mendieta-Moreno and P L de Andrés and E Tosi and J A Martín-Gago and J M Cuerva and I Palacio and A G Campaña and C Sánchez-Sánchez},
  journal = {Journal of the American Chemical Society},
  year = {2026},
  month = oct,
  doi = {10.1021/jacs.6c08825},
  url = {https://europepmc.org/article/MED/42954538},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - On-Surface Synthesis of a Low Bandgap Cyclopenta[c,d]azulene-Based Polymer.
AU  - S Jiménez-Fernández
AU  - F Villalobos
AU  - V Kumar
AU  - J I Martínez
AU  - J I Mendieta-Moreno
AU  - P L de Andrés
AU  - E Tosi
AU  - J A Martín-Gago
AU  - J M Cuerva
AU  - I Palacio
AU  - A G Campaña
AU  - C Sánchez-Sánchez
PY  - 2026
DA  - 2026/10/01
JO  - Journal of the American Chemical Society
DO  - 10.1021/jacs.6c08825
UR  - https://europepmc.org/article/MED/42954538
AB  - Nonbenzenoid topologies offer a compelling strategy to tailor the electronic properties of low-dimensional carbon materials. Here, we report the on-surface synthesis of a nonalternant polymer incorporating a [7-5-5] cyclopenta[c,d]azulene (CPA) motif on Au(111) via thermally induced Ullmann coupling. Bond-resolved scanning tunneling microscopy confirms the robustness of the [7-5-5] framework. Scanning tunneling spectroscopy, together with dI/dV mapping supported by density functional theory calculations, reveals a remarkable narrow polymeric bandgap of 1.5 eV. The electronic structure is governed by the intramolecular charge transfer from the heptagonal ring to the adjacent fused pentagonal rings, resulting in a pronounced dipole moment despite being composed exclusively of carbon and hydrogen. Aromaticity analyses indicate the coexistence of locally aromatic and slightly antiaromatic regions, highlighting the intrinsic electronic frustration associated with the nonalternant topology. These findings demonstrate how the controlled incorporation of [7-5-5] motifs enables the rational bandgap engineering in carbon-based polymers and expands the scope of nonbenzenoid design in on-surface synthesis.
SN  - 0002-7863
SN  - 1520-5126
ER  -