164991-12-2Relevant academic research and scientific papers
A Novel "Double-Coupling" Strategy for Iterative Oligothiophene Synthesis Using Orthogonal Si/Ge Protection
Spivey, Alan C.,Turner, David J.,Turner, Michael L.,Yeates, Stephen
, p. 1899 - 1902 (2002)
(Matrix Presented) A new iterative synthesis of regioregular oligothiophenes has been developed in which "double-coupling" after each iteration minimizes deletion sequences. The method exploits the susceptibility of α-silyl- but not α-germyl-substituted thiophene derivatives toward nucleophilic ipso-protodemetalation and features an unusual "base-free" Suzuki-type cross-coupling protocol. The strategy has been designed for the solid-phase synthesis of high purity oligothiophenes using a germanium-based linker.
Organic pi-conjugated compound, and preparation method and application thereof
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Paragraph 0181; 0182; 0183, (2017/01/17)
The invention provides an organic pi-conjugated compound including: a spiro-[4,4]-4-nonatetraene or 5,5-a-spiro-[4,4]-nonatetraene unit; a molecular fragment unit which is connected with a C=C double bond in the spiro-[4,4]-4-nonatetraene or 5,5-a-spiro-[4,4]-nonatetraene unit to form a five-membered aromatic heterocyclic ring or multi-membered aromatic fused ring structure; a short-chain conjugated unit which forms pi-conjugated connection with the molecular fragment unit by a C-C single bond; and a terminal group connected with the short-chain conjugated unit, wherein the short-chain conjugated unit is formed by connecting 1-12 aromatic rings or aromatic heterocyclic rings or aromatic fused rings in series in a manner of pi-conjugated connection. The invention also provides a preparation method of the organic pi-conjugated compound. The compound provided by the invention has good solubility and higher electron transmission performance, also has the advantages of clear structure, easily purified materials, better repeatable performance and the like, and has wide application prospects in organic semiconductor devices, especially in organic photoelectronic devices.
Towards a general solid phase approach for the iterative synthesis of conjugated oligomers using a germanium based linker - First solid phase synthesis of an oligo-(triarylamine)
Turner, David J.,Anemian, Remi,MacKie, Philip R.,Cupertino, Domenico C.,Yeates, Stephen G.,Turner, Michael L.,Spivey, Alan C.
, p. 1752 - 1763 (2008/02/10)
The development of a germanium-based linker system for the solid phase synthesis (SPS) of 3-(n-hexyl)thiophene oligomers and the first SPS of triarylamine oligomers via iterative chain extension is described. The efficiency of the key steps in the oligomer syntheses and their compatibility with the germanium linker are demonstrated by the SPS of bi-[3-(n-hexyl) thiophene] 19 and ter-(triarylamine) 50. The use of a germanium-based linker in combination with appropriately selected silicon-based blocking/protecting groups allows double coupling to drive the key cross coupling steps to completion hence minimising deletion sequences and also allows for traceless and potentially functionalisative cleavage from the resin. The latter feature has yet to be fully explored but towards this end the first ipso-borodegermylation reaction of a 2-germyl-3-(n-hexyl)thiophene is presented. The Royal Society of Chemistry.
A Tuneable Ge-based Linker that Enables Application-led Solid Phase Synthesis Optimisation - Towards a Robust Iterative Synthesis of Oligothiophenes
Spivey, Alan C.,Turner, David J.,Turner, Michael L.,Yeates, Stephen
, p. 111 - 115 (2007/10/03)
A convenient synthesis of a new dichlorogermanium-based linker-precursor for solid phase synthesis is described that allows facile introduction of a range of 'spectator' substituents (R) onto germanium. Variation of these R groups allows modulation of the stability of the key germanium-carbon bond between the linker and the aryl library. The tuning process is exemplified by application to the optimisation of a linker for the iterative solid-phase synthesis (SPS) of oligothiophenes.
