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Title: New AAA-DDD heterocomplexes
Author: Djurdjevic, Smilja
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2007
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The basis of this project was to synthesise novel aromatic heterocyclic hosts, with two and three adjacent hydrogen bond acceptor (A) sites in AA and AAA arrangements. In order to produce the targeted systems, new synthetic methods and techniques such as flash vacuum pyrolysis (FVP), Buchwald-Hartwig-coupling and Suzuki coupling chemistry, etc. were employed. The purpose of this investigation was to study the binding affinity of the AA and AAA units with donors (D) in AA-DDD and AAA-DDD heterocomplexes. The FVP approach allowed the synthesis of naphthydrine ring systems in only two steps from substituted Meldrum’s acid derivatives after cyclisations at high temperature. In the second approach palladium catalyzed coupling was used to provide heterocyclic diarylamines from readily available pyridine or naphthyridine precursors, with subsequent ring closure under acidic conditions. This approach led to the synthesis of new compounds: dipyrido[1,2-a;2’, 3’-a]pyrimidin-5-one (AA) and 1,6a,11,12-tetraaza-naphthacene-6-one (an AAA hydrogen bonding unit) in high yields. The Suzuki coupling strategy afforded compounds: dibenzo[c,f][1,8]naphthyridine 6 (AA) and 1,13,14-triazadibenz[a,j]anthracene (AAA); their extended aromatic framework is thought to help overcome stability problems during binding studies. For the binding studies, the selected DDD counterparts were dihydropyridines 2,6-bis(hydroxyl-methyl)-p-cresol and protonated 2,6-diaminopyridine (with a lipophylic tetraarylborate counter-ion) developed as a cationic DDD unit. The extremely high binding stability of all these heterocomplexes is attributed to the combination of cooperative secondary interactions and strong electrostatic energy.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available