Propeller-shaped molecules with a thiazole hub: structural landscape and hydrazone cap mediated tunable host behavior in 4-hydrazino-1,3-thiazolesElectronic supplementary information (ESI) available. CCDC reference numbers 1002352, 1002353, 1052981, 1052982, 1052983. See DOI: 10.1039/c5ce01042j

• Main Authors: Titus, Sarah, Sreejalekshmi, Kumaran G
• Format: Article
• Language: English
• ISSN: 1466-8033
• DOI: 10.1039/c5ce01042j

Propeller-shaped molecules with 2,4,5-trisubstituted-1,3-thiazole as the hub and tunable blades ( B 1 - B 3 ) were synthesized as trivariant scaffolds. B 1 - B 3 were modulated by varying the hydrazone capping in B 1 , the isothiocyanate in B 2 and the α-haloketone in B 3 and the structural landscapes examined. Multicomponent molecular crystals formed nitrogen rich channels (NRCs) of varied shapes and dimensions which were largely steered by the substitution pattern in B 1 and established by varying carbonyl components. Isopropylidene derivatives (IPHAT) stabilized single file water inside the NRC (~34 Å 2 ) between B 1 and B 2 , benzylidene derivatives (BzHAT) formed a constricted NRC and accommodated solvates inside a hydrophobic cavity between B 1 and B 3 whereas a pincer-shaped NRC devoid of guest molecules was formed by cyclohexylidene derivatives (CyHAT). The hydrazone substituent-driven variation in solid state landscapes indicates a wide scope of expandability of these thiazole templates as supramolecular synthons for tunable hosts. Propeller-shaped molecules with 2,4,5-trisubstituted-1,3-thiazole as the hub and tunable blades ( B 1 - B 3 ) were synthesized as trivariant scaffolds.