Abstract
The high-yield synthesis and the structural investigation of a new cryptand with C3 symmetry, exhibiting 2,4,6-triphenyl-1,3,5-triazine central units and pyridine-based bridges, are reported. The structure of the compound was investigated by single crystal X-ray diffractometry, NMR (nuclear magnetic resonance), HRMS (high resolution mass spectrometry) measurements, and theoretical calculations. The study of supramolecular behavior in solid state revealed the association of cryptand molecules by C-H---π and π---π contacts. Moreover, theoretical calculations indicated the high binding affinity of the cryptand for various organic molecules as guests.
Highlights
Cryptands exhibiting C3 symmetry have been exciting synthetic targets, due to their high ability to form stable “host–guest” supramolecular assemblieseither with ions [2,3,4] or neutral organic molecules [5,6,7,8,9]
We investigated several C3 cryptands (Scheme 1, 1–3) exhibiting 1,3,5-triazine or 2,4,6-triphenyl-1,3,5-triazine central aromatic units
The structural investigation of cryptand 4 was carried out using NMR, HRMS, and single crystal X-ray diffractometry
Summary
Cryptands exhibiting C3 symmetry have been exciting synthetic targets, due to their high ability to form stable “host–guest” supramolecular assemblies (i.e., as result of the macrobicyclic effect [1])either with ions (cations and anions) [2,3,4] or neutral organic molecules [5,6,7,8,9]. 1,3,5-trisubstituted benzene [10,11,12,13,14], 2,4,6-trisubstituted-1,3,5-triazine [15,16,17], tertiary amines [18,19], or phosphines [20,21], as well as cyclotribenzylene [22,23,24] as central units, connected by various bridges, such as oligoethyleneoxide [25,26], di-yne [17,27,28], pyridine [29,30,31], or triazole [32,33,34,35], in agreement with the employed macrocyclization procedure, have been reported and showed good binding abilities for various guests. We investigated several C3 cryptands (Scheme 1, 1–3) exhibiting 1,3,5-triazine or 2,4,6-triphenyl-1,3,5-triazine central aromatic units. Compounds 2(a–c) exhibit a high affinity for alkali (Na+ , K+ ) and ammonium cations (e.g., dication of 1,5-naphthalenediamine).
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