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Pyrrole-Embedded Linear and Helical Graphene Nanoribbons
Dandan Miao1, Vanessa Di Michele2, Félix Gagnon1
1Département de chimie and Centre de Recherche sur les Matériaux Avancés (CERMA), Université Laval, 1045 Ave de la Médecine, Québec, Canada G1V 0A6.
Journal of the American Chemical Society
|July 23, 2021
Summary
New graphene nanoribbons (L-PyGNR and H-PyGNR) with electron-rich pyrrole units were synthesized. These materials exhibit excellent conductivity and fluorescence sensing capabilities for TNT detection.
Area of Science:
- Materials Science
- Organic Chemistry
- Nanotechnology
Background:
- Graphene nanoribbons (GNRs) are promising materials for electronic applications.
- Incorporating electron-rich units can tune GNR properties.
- Pyrrole units offer potential for enhanced electronic and optical characteristics.
Purpose of the Study:
- To synthesize linear and helical polypyrrole-based graphene nanoribbons (L-PyGNR and H-PyGNR).
- To investigate the electronic and optical properties of the synthesized GNRs.
- To evaluate their potential for conductivity and sensing applications.
Main Methods:
- Photochemical cyclodehydrochlorination (CDHC) reaction for synthesis.
- Characterization of electronic and optical properties, including bandgap and HOMO levels.
- Measurement of thin-film conductivity using the four-point method.
- Evaluation of fluorescence sensing capabilities for TNT detection.
Main Results:
- Successful synthesis of L-PyGNR and H-PyGNR with electron-rich pyrrole units.
- Achieved moderate bandgap values and high HOMO energy levels due to pyrrole incorporation.
- Cyclization planarization reduced bandgap by approximately 0.5 eV compared to polypyrrole.
- Measured conductivity up to 0.12 S/cm for chemically oxidized L-PyGNR.
- Demonstrated excellent fluorescence sensing for TNT with high Stern-Volmer constants (Ksv up to 6.4 × 10^6 M^-1).
Conclusions:
- The synthesized L-PyGNR and H-PyGNR possess tunable electronic properties owing to pyrrole units.
- These GNRs exhibit promising conductivity for electronic applications.
- The materials show excellent potential as fluorescent sensors for explosives like TNT.

