NDLI: A Fully Conjugated TTF–π–TCAQ System: Synthesis, Structure, and Electronic $Properties^{†}$

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A Fully Conjugated TTF–π–TCAQ System: Synthesis, Structure, and Electronic $Properties^{†}$

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A Fully Conjugated TTF–π–TCAQ System: Synthesis, Structure, and Electronic $Properties^{†}$

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Martín, Nazario Viruela, Rafael Spänig, Fabian Carretero, Juan C. Santos, José Adrio, Javier Ortí, Enrique Guldi, Dirk M. Illescas, Beatriz M.
Description	Author Affiliation: Santos J ( Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense, Ciudad Universitaria, 28040 Madrid, Spain.)
Abstract	The synthesis of the first fully conjugated tetrathiafulvalene–tetracyano-p-quinodimethane ((TTF)–TCNQ)-type system has been carried out by means of a Julia–Kocienski olefination reaction. In particular, a tetracyanoanthraquinodimethane (TCAQ) formyl derivative and two new sulfonylmethyl-exTTFs (exTTF=2-[9-(1,3-dithiol-2-ylidene)anthracen-10(9H)-ylidene]-1,3-dithiole)—prepared as new building blocks—were linked. A variety of experimental conditions reveal that the use of sodium hexamethyldisilazane (NaHMDS) as base in THF afforded the E olefins with excellent stereoselectivity. Theoretical calculations at the B3LYP/6-31G** level point to highly distorted exTTF and TCAQ that form an almost planar stilbene unit between them. Although calculations predicted appreciable electronic communication between the donor and the acceptor, cyclic voltammetric studies did not substantiate this effect. It was only in photophysical assays that the electronic communication emerged in the form of a charge-transfer (CT) absorption and emission. Once photoexcited (i.e., the locally excited state or excited charge-transfer state), an ultrafast, subpicosecond charge separation leads to a radical ion pair state in which the spectroscopic features of the radical cation of exTTF as well as the radical anion of TCAQ are discernable. The radical ion pair is metastable and undergoes a fast ((1.0±0.2) ps) charge recombination to reconstitute the electronic ground state. Such ultrafast charge separation and recombination processes come as a consequence of the very short vinyl linkage between the two electroactive units.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	10
Volume Number	17
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2011-03-01
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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