Design and Synthesis of Aviram-Ratner-Type Dyads and Rectification Studies in Langmuir-Blodgett (LB) Films

Download

index.pdf

Date

2016-07-18

Author

JAYAMURUGAN, Govindasamy
GOWRI, Vijayendran
HERNANDEZ, David
MARTIN, Santiago
Gonzalez-Orive, Alejandro
Dengiz, Çağatay
DUMELE, Oliver
PEREZ-MURANO, Francesc
GISSELBRECHT, Jean-Paul
BOUDON, Corinne
SCHWEIZER, W. Bernd
BREITEN, Benjamin
FINKE, Aaron D.
JESCHKE, Gunnar
BERNET, Bruno
RUHLMANN, Laurent
CEA, Pilar
DIEDERICH, Francois

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

153
views

230
downloads

The design and synthesis of Aviram-Ratner-type molecular rectifiers, featuring an anilino-substituted extended tetracyanoquinodimethane (exTCNQ) acceptor, covalently linked by the sigma-spacer bicyclo[2.2.2]octane (BCO) to a tetrathiafulvalene (TTF) donor moiety, are described. The rigid BCO spacer keeps the TTF donor and exTCNQ acceptor moieties apart, as demonstrated by X-ray analysis. The photophysical properties of the TTF-BCO-exTCNQ dyads were investigated by UV/Vis and EPR spectroscopy, electrochemical studies, and theoretical calculations. Langmuir-Blodgett films were prepared and used in the fabrication and electrical studies of junction devices. One dyad showed the asymmetric current-voltage (I-V) curve characteristic for rectification, unlike control compounds containing the TTF unit but not the exTCNQ moiety or comprising the exTCNQ acceptor moiety but lacking the donor TTF part, which both gave symmetric I-V curves. The direction of the observed rectification indicated that the preferred electron current flows from the exTCNQ acceptor to the TTF donor.

Subject Keywords

[2+2] cycloaddition-retroelectrocyclization, Aviram-Ratner dyad, Charge transfer, Langmuir-Blodgett films, molecular electronics materials

URI

https://hdl.handle.net/11511/47768

Journal

CHEMISTRY-A EUROPEAN JOURNAL

DOI

https://doi.org/10.1002/chem.201505216

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Design and synthesis of novel substituted indole-acrylamide derivatives and evaluation of their anti-cancer activity as potential tubulin-targeting agents Hawash, Mohammed; Kahraman, Deniz Cansen; OLĞAÇ, ABDURRAHMAN; Ergun, Sezen Guntekin; Hamel, Ernest; Cetin-Atalay, Rengul; BAYTAŞ, SULTAN (2022-04-01) Novel compounds containing polar and nonpolar substitutions on the prop-2-en-1-on linker of the trans-indol-3-ylacrylamide scaffold were designed by modeling within the colchicine site of tubulin and then synthesized to determine the role of such substitutions on tubulin polymerization. We first determined the in vitro antiproliferation activities of the compounds against cancer cell lines with a particular focus on hepatocellular carcinoma. The results indicated that five of the compounds showed moderate a...
Synthesis, spectroscopic and electrochemical studies of perylene containing conjugated copolymers Bayseç, Şebnem; Toppare, Levent Kamil; Yılmaz, Levent; Department of Polymer Science and Technology (2013) The synthesis , spectroscopic and electrochemical properties of a series of donor-acceptor (DA) type polymers by changing the donor unit (thiophene, dithienopyrrole) polymer backbone were investigated.The synthesized CoP1 and CoP2 were designed to investigate the effect of copolymerization and insertion of perylene tetracarboxylic dimide (PDI) on the structure of benzotriazole (BTz) based polymers. For CoP1 1,7-dibromo-perylene diimide,4,7-dibromo-2-dodecyl-2H-benzo[d][1,2,3]triazole and 2,5 bis(tributylsta...
Design, fabrication and characterization of novel metamaterials in microwave and terahertz regions : multi-band, frequency-tunable and miniaturized structures Ekmekçi, Evren; Sayan, Gönül; Department of Electrical and Electronics Engineering (2010) This dissertation is focused on the design, fabrication, and characterization of novel metamaterials in microwave and terahertz regions with the following outcomes: A planar µ-negative metamaterial structure, called double-sided SRR (DSRR), is proposed in the first part of this study. DSRR combines the features of a conventional split ring resonator (SRR) and a broadside-coupled SRR (BC-SRR) to obtain much better miniaturization at microwave frequencies for a given physical cell size. In addition to DSRR, d...
Use of purified and modified bentonites in linear low-density polyethylene/organoclay/compatibilizer nanocomposites Seyidoglu, Tijen; Yılmazer, Ülkü (2012-05-05) Polyethylene-based ternary nanocomposites were prepared with different clay structures, obtained by the modification of purified Resadiye bentonite as the reinforcement, a random terpolymer of ethylene, butyl acrylate, and maleic anhydride with the trade name Lotader3210 as the compatibilizer, and linear low-density polyethylene (LLDPE) as the polymer matrix in an intensive batch mixer. The quaternary ammonium/phosphonium salts used for the modification of bentonite were dimethyldioctadecyl ammonium (DMDA) ...
Synthesis and Optoelectronic Properties of Janus-Dendrimer-Type Multivalent Donor Acceptor Systems Dengiz, Çağatay; GISSELBRECHT, Jean-Paul; BOUDON, Corinne; TRAPP, Nils; SCHWEIZER, W. Bernd; DIEDERICH, Francois (2015-01-16) A convergent, multistep protocol was employed for the synthesis of a Janus-type multivalent donoracceptor system. The synthetic approach is based on a Sonogashira cross-coupling of two differently ferrocene-(Fc) substituted dendrons and a final sixfold [2 + 2] cycloaddition-retroelectrocyclization (CA-RE) reaction with tetracyanoethene, which occurs regioselectively at only one of the rigidly linked dendrons. The structural and optoelectronic properties of the compounds were investigated by X-ray analysis, ...

Citation Formats

G. JAYAMURUGAN et al., “Design and Synthesis of Aviram-Ratner-Type Dyads and Rectification Studies in Langmuir-Blodgett (LB) Films,” CHEMISTRY-A EUROPEAN JOURNAL, pp. 10539–10547, 2016, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/47768.