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Donor-Acceptor dyads for molecular r...

Kondratenko, Mykola.

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Donor-Acceptor dyads for molecular rectifying devices.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Donor-Acceptor dyads for molecular rectifying devices./
Author:	Kondratenko, Mykola.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2011,
Description:	249 p.
Notes:	Source: Dissertations Abstracts International, Volume: 74-02, Section: B.
Contained By:	Dissertations Abstracts International74-02B.
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=NR78655
ISBN:	9780494786550

Donor-Acceptor dyads for molecular rectifying devices.
Kondratenko, Mykola.

Donor-Acceptor dyads for molecular rectifying devices. - Ann Arbor : ProQuest Dissertations & Theses, 2011 - 249 p.

Source: Dissertations Abstracts International, Volume: 74-02, Section: B.

Thesis (Ph.D.)--McGill University (Canada), 2011.

This item must not be sold to any third party vendors.

The interest in molecular electronics began in the 1970s with the work of Aviram and Ratner, who proposed that a donor-acceptor dyad, specifically TTF-σ-TCNQ molecule (TTF-tetrathiafulvalene, σ-nonconjugated bridge and TCNQ-tetracyanoquinodimethane), can resemble the electric properties of a p-n junction, acting as a unimolecular diode. The reason of such behaviour lies in asymmetrically distributed electronic levels, and very low HOMO-LUMO gap (0.3 eV) that was imposed for the model molecule. Up to date, numerous donor-acceptor dyads were investigated as candidates for molecular rectifiers, which included some D-σ-A dyads with weak or moderate donor and acceptor moieties, numerous D-π-A and also molecules without obvious asymmetry in the electronic structure. However, neither the original TTF-σ-TCNQ molecule nor any other molecule with similar HOMO-LUMO gap have been studied in molecular electronics applications, which was due to synthetic unavailability of such molecules. In this thesis we present molecular design, synthesis as well as characterization of series of Donor-Acceptor dyads with different combinations of well studied electroactive moieties (TTF-σ-fluorene, nEDOT-3CNQ, nEDOT-NDI). Herein we describe our progress towards the main synthetic challenge in the field of molecular rectifiers - coupling together strong donor and strong acceptor molecules. To achieve this we employed different synthetic strategies, namely, use of intermediates with moderated redox properties and highly reactive derivatives to avoid formation of charge-transfer complexes between donor and acceptor as well as utilization of the donor-acceptor complexation which results their in covalent binding. The synthetic design includes two types of approaches allowing binding the dyad molecules to electrode surface: (1) amphiphilic structure which enables deposition of molecular monolayers via Langmuir-Blodgett technique and (2) thiol/disulfide functionality suitable for covalent grafting of molecules to metals. Characterization of such monolayers by different spectroscopic and electrochemical techniques as well as analysis of the alignment and packing of the molecules within the films as well as monolayers stability is discussed. Finally, we describe fabrication of Electrode/Organic monolayer/Electrode junctions and discuss results of the charge transport measurements of the synthesized donor-acceptor dyads.

ISBN: 9780494786550Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

Donor-acceptor dyads

Donor-Acceptor dyads for molecular rectifying devices.
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520 $a The interest in molecular electronics began in the 1970s with the work of Aviram and Ratner, who proposed that a donor-acceptor dyad, specifically TTF-σ-TCNQ molecule (TTF-tetrathiafulvalene, σ-nonconjugated bridge and TCNQ-tetracyanoquinodimethane), can resemble the electric properties of a p-n junction, acting as a unimolecular diode. The reason of such behaviour lies in asymmetrically distributed electronic levels, and very low HOMO-LUMO gap (0.3 eV) that was imposed for the model molecule. Up to date, numerous donor-acceptor dyads were investigated as candidates for molecular rectifiers, which included some D-σ-A dyads with weak or moderate donor and acceptor moieties, numerous D-π-A and also molecules without obvious asymmetry in the electronic structure. However, neither the original TTF-σ-TCNQ molecule nor any other molecule with similar HOMO-LUMO gap have been studied in molecular electronics applications, which was due to synthetic unavailability of such molecules. In this thesis we present molecular design, synthesis as well as characterization of series of Donor-Acceptor dyads with different combinations of well studied electroactive moieties (TTF-σ-fluorene, nEDOT-3CNQ, nEDOT-NDI). Herein we describe our progress towards the main synthetic challenge in the field of molecular rectifiers - coupling together strong donor and strong acceptor molecules. To achieve this we employed different synthetic strategies, namely, use of intermediates with moderated redox properties and highly reactive derivatives to avoid formation of charge-transfer complexes between donor and acceptor as well as utilization of the donor-acceptor complexation which results their in covalent binding. The synthetic design includes two types of approaches allowing binding the dyad molecules to electrode surface: (1) amphiphilic structure which enables deposition of molecular monolayers via Langmuir-Blodgett technique and (2) thiol/disulfide functionality suitable for covalent grafting of molecules to metals. Characterization of such monolayers by different spectroscopic and electrochemical techniques as well as analysis of the alignment and packing of the molecules within the films as well as monolayers stability is discussed. Finally, we describe fabrication of Electrode/Organic monolayer/Electrode junctions and discuss results of the charge transport measurements of the synthesized donor-acceptor dyads.
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