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The method includes three steps: Pd-catalyzed Suzuki—Miyaura reaction, hydrolysis under basic conditions and Cu-catalyzed N-arylation.

Monolithiation of tetrathiafulvalene (2-(1,3-dithiol-2-ylidene)-1,3-dithiole, TTF) followed by reaction with the appropriate p-toluenesulphonyl halide yields monochloro-, monobromo- and monoiodo-TTF (34-48 % yield); tetrachloro-TTF is obtained in 30 % yield by tetralithiation of TTF followed by addition of p-toluenesulphonyl chloride. Cyclic voltammetric data establish that the oxidation potential of TTF is significantly increased upon halogenation.

The reaction of mono-lithiated tetrathiafulvalene (TTF) with elemental sulfur or elemental selenium at –78 °C yields the transient species TTF-S– Li+ and TTF-Se– Li+, respectively, which have been trapped with a range of alkyl halides to yield new alkylthio- and alkylseleno-TTF derivatives. Reaction of the TTF-thiolate anion with 2-bromoethanol yields 4-(2-hydroxyethylthio)tetrathiafulvalene which is a particularly versatile building block for the synthesis of a range of new mono-functionalised TTF derivatives containing ether, ester, acrylate, urethane and vinylthio groups in the side chain. Onepot syntheses of ethylenedithio-TTF (EDT-TTF) and ethylenediseleno-TTF (EDS-TTF) from TTF are reported. The structure of EDS-TTF has been determined by single crystal X-ray analysis which reveals dimers with molecular planes orthogonal to each other.

Cyanotetrathiafulvalenes were prepd. conveniently and in good yield from tetrathiafulvalenylithium intermediates. 4-Cyanotetrathiafulvalene (I) was used as a building block to synthesize new derivs. with potentially interesting solid-state structures. The x-ray crystal structure of I revealed that neither H-bonding interactions nor CN-CN dipole interactions are implicated in the overall packing. [on SciFinder(R)]

The synthesis and characterisation of the first discotic liquid crystalline tetrathiafulvalenylphthalocyanine is described.

Unsymmetrical monohydroxypentaalkoxytriphenylenes have been conveniently prepared from the readily accessible symmetrical hexa-alkyloxytriphenylenes using boron tribromide mediated ether cleavage.

Hydrogen bonded interactions are among the most important non-covalent interactions in supramolecular chemistry. The strength, selectivity and directionality inherent in hydrogen bonding processes have allowed the creation of complex and efficient molecular hosts capable of selective binding to a wide variety of complementary guests. Major advances in controlling host-guest complexation have occurred in the last decade, principally through systematic modification of the electrostatic properties and/or geometry of the hosts, thereby fine-tuning the molecular recognition event. More recently, systems have been developed which allow the effectiveness and selectively of hydrogen bonding interactions to be reversibly modulated by an external stimulus, more accurately mimicking biological systems and providing building blocks for the construction of novel advanced materials, sensors and devices. In this review, we highlight some of the methods available for modulating the strength and selectivity of hydrogen bonded interactions in synthetic host-guest systems.

The synthesis, electrochemistry and mesogenic properties of novel anthraquinolyl–triphenylenes are described. 1H NMR, UV–vis, solution electrochemistry and molecular modelling studies indicate that an intermolecular charge–transfer interaction occurs between the anthraquinone moiety and the triphenylene nucleus.

Monolithiotetrathiafulvalene reacts with the acyl chlorides (IIa) and (IIb), hexadecyl chlorothioformate (IIc), or trimethylsilyl chloride (IId) to produce the monosubstituted tetrathiafulvalenes (IIIa) -(IIId).