An unconventional route to an ambipolar azaheterocycle and its in situ generated radical anion

Autor:	Chandan Kumar, Himadri S. Karmakar, Parameswar Krishnan Iyer, A.K. Mandal, Sayan Bhattacharyya, Somnath Dey, Anjan Bedi, Smruti Ranjan Sahoo, Sanjio S. Zade, Nani Gopal Ghosh, Sarasija Das, Anwesha Choudhury
Rok vydání:	2021
Předmět:	Cyclopentadienyl anion Fullerene Ambipolar diffusion Chemical shift Organic Chemistry Electron Biochemistry Space charge Ion chemistry.chemical_compound chemistry Chemical physics Physical and Theoretical Chemistry Cyclopentane
Zdroj:	Organic & Biomolecular Chemistry. 19:5114-5120
ISSN:	1477-0539 1477-0520
DOI:	10.1039/d1ob00826a
Popis:	Herein we report the synthesis, characterization and application of an azaheterocycle 4 obtained via an unprecedented C–N coupling. The neutral azaheterocycle undergoes one-electron reduction to form an air-stable radical anion in situ, which provides added benefit towards operational stability of the device during n-type charge transport. The unusual stability of this radical anion is due to the fact that the fused cyclopentane ring upon reduction forms aromatic cyclopentadienyl anion, and the negative charge delocalizes over the nearly planar azaheterocycle core. The present azaheterocycle can be considered as a mimic of a fullerene fragment, which shows balanced ambipolar charge transport in space charge limited current (SCLC) devices with moderate hole (μh) and electron (μe) mobilities (μh = 2.96 × 10−3 cm2 V−1 s−1 and μe = 1.11 × 10−4 cm2 V−1 s−1). Theoretical studies such as nucleus independent chemical shifts (NICS) calculations, anisotropy of the induced current density (ACID) plots, spin density mapping and anisotropic mobility calculations were performed to corroborate the experimental findings.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f5fba4eac9a4df57a668de1c642e5140 https://doi.org/10.1039/d1ob00826a Zobrazit plný text záznamu