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One of us (AJS) was fortunate enough to have known Professor George Gray during his final years of teaching at the University of Hull. In 1989, I was finishing my undergraduate studies when I sat in George's class entitledProteins and Polypeptides. I was in awe of George, as were all students in the class, but struck by his down-to-earth demeanour, warmth, approachability and his soft Scottish accent (I still have the notes I took from his class). George was a truly inspirational teacher to everyone who knew him and I consider it a great privilege to have known him. During my time at Hull I became fascinated with thiophene-containing liquid crystals, my interest being strongly influenced by George Gray, Ken Toyne and Mike Scrowston. This manuscript is my small tribute to George and it describes our new methodological developments in the synthesis of low molar mass liquid crystals that contain the thieno[3,2-b]thiophene and thieno[2,3-b]thiophene cores. [ABSTRACT FROM PUBLISHER]

A series of alkyl 5-(4-alkoxyphenyl)thieno[3,2-b]thiophene-2-carboxylates were prepared via a direct, efficient Pd(0)-catalysed Suzuki–Miyaura coupling approach. A series of long-chain alkyl thieno[3,2-b]thiophene-2-carboxylate esters, synthesised from newly reported alkyl mercaptoacetates, were elaborated into the target compounds via regioselective (C-5) halogenation followed by cross-coupling with 4-alkoxyphenyltrifluoroborate salts. As expected, these target alkyl 5-(4-alkoxyphenyl)thieno[3,2-b]thiophene-2-carboxylate ester mesogens exhibited the orthogonal smectic A phase; notably, they are the first materials built on the thieno[3,2-b]thiophene motif to also exhibit the smectic C mesophase. [ABSTRACT FROM AUTHOR]