[4]Cyclo-N-ethyl-2,7-carbazole Synthesis, structural, electronic and charge transport properties

Fabien Lucas 1 Lambert Sicard 1 Olivier Jeannin 1 Joëlle Rault-Berthelot 1 Emmanuel Jacques 2 Cassandre Quinton 1 Cyril Poriel 1
1 ISCR - Institut des Sciences Chimiques de Rennes
2 IETR - Institut d'Electronique et de Télécommunications de Rennes
Abstract : Nanorings, which are macrocycles possessing radially directed π-orbitals have shown fantastic development in the last ten years. Unravelling their unusual electronic properties has been one of the driving forces of this research field. However, and despite promising properties, their incorporation in organic electronic devices remains very scarce. In this work, we aim to contribute to bridge the gap between organic electronics and nanorings by reporting the synthesis, the structural and electronic properties and the incorporation in an organic field-effect transistor (OFET) of a cyclic tetracarbazole, namely [4]cyclo-N-ethyl-2,7-carbazole ([4]C-Et-Cbz). The structural, photophysical and electrochemical properties have been compared to those of structurally related analogues [4]cyclo-9,9-diethyl-2,7-fluorene [4]C-diEt-F (with carbon bridges) and [8]-cycloparaphenylene [8]CPP (without any bridge) in order to shed light on the impact of the bridging in nanorings. This work shows that nanorings can be used as an active layer in an OFET and provides a first benchmark in term of OFET characteristics for this type of molecules.
Keywords : organic semiconductors organic field effect transistor nanoring Charge Transport Structure-Properties Relationship bridged cyclo-oligophenylenes
Document type :
Journal articles
Complete list of metadatas

Cited literature [60 references]  Display  Hide  Download
https://hal-univ-rennes1.archives-ouvertes.fr/hal-02120749
Contributor : Laurent Jonchère <>
Submitted on : Thursday, July 18, 2019 - 11:05:18 AM
Last modification on : Thursday, July 18, 2019 - 4:06:54 PM

File

Poriel et al-2019-[4]Cyclo-N-e...
Files produced by the author(s)

Identifiers

Collections

UNIV-RENNES1 | UNIV-NANTES | UNIV-RENNES | UR1-UFR-ISTIC | UR1-UFR-SPM | INC-CNRS | ISCR | IETR | INSA-GROUPE

Citation

Fabien Lucas, Lambert Sicard, Olivier Jeannin, Joëlle Rault-Berthelot, Emmanuel Jacques, et al.. [4]Cyclo-N-ethyl-2,7-carbazole Synthesis, structural, electronic and charge transport properties. Chemistry - A European Journal, Wiley-VCH Verlag, 2019, 25 (32), pp.7740-7748. ⟨10.1002/chem.201901066⟩. ⟨hal-02120749⟩

Export

BibTeX TEI DC DCterms EndNote

Share

Metrics

Record views

58

Files downloads

16