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- Title
The Effect of TCNE and TCNQ Acceptor Units on Triphenylamine-Naphthalenediimide Push-Pull Chromophore Properties.
- Authors
Rao, Pedada Srinivasa; Brixi, Samantha; Shaikh, Dada B.; Al Kobaisi, Mohammad; Lessard, Benoît H.; Bhosale, Sidhanath V.; Bhosale, Sheshanath V.
- Abstract
Asymmetrical and symmetrical push-pull chromophore-based on triphenylamine (TPA) donors and naphthalenediimide (NDI) acceptors are designed and successfully synthesized via [2+2] cycloaddition-retroelectrocyclization (CA-RE) reaction with wellknown electron-accepting tetracyanoethylene (TCNE) and 7,7,8,8, -tetracyanoquinodimethane (TCNQ) groups. The novel series of compounds NDI-TPA-1 to NDI-TPA-6 were characterized to identify the influence of the TCNE and TCNQ π-conjugated linkers on the optical, electrochemical, and electronic properties of these molecules. We found that in dichloromethane the NDI-TPAs 1, 4, 5, and 6 display absorbance peaks at increasing wavelengths 605, 641, 646, and 645 nm, respectively. We demonstrated that through simple chemical modification we could drop the lowest occupied molecular orbital of NDI-TPA-1 to 6. Furthermore, NDI-TPA-1 to 6 were integrated into organic thin-film transistors (OTFTs) via spincoating technique, and charge transfer properties were investigated. We found that the choice of the functional group led to either p-type, n-type, or ambipolar characteristics.
- Subjects
TRIPHENYLAMINE; MOLECULAR orbitals; CHARGE transfer; TETRACYANOETHYLENE; FUNCTIONAL groups; TRANSISTORS; DIARYLETHENE
- Publication
European Journal of Organic Chemistry, 2021, Vol 2021, Issue 18, p2615
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202100198