Synthesis and structure of upper-rim 1,3-alternate tetraoxacalix[2]arene[2]triazine azacrowns and change of cavity in response to fluoride anion.
The upper-rim 1,3-alternate tetraoxacalix[2]arene[2]triazine azacrowns were constructed effectively by macrocyclic condensation reaction of diamines with dichlorinated tetraoxacalix[2]arene[2]triazine intermediates that were synthesized from the stepwise fragment coupling reactions of 3,5-dihydroxybenzoic acid esters with cyanuric chlorides. Because of the formation of conjugation of amino groups with triazine rings, tetraoxacalix[2]arene[2]triazine azacrowns existed in a mixture of syn- and anti-isomeric forms. Both fluorescence titration and 1H NMR spectroscopic study showed that tetraoxacalix[2]arene[2]triazine azacrowns interacted with fluoride anion, leading to cavity changes of the host molecules.
Hou
Bao-Yong
BY
Beijing National Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100080, China.
Wang
De-Xian
DX
Yang
Hai-Bo
HB
Zheng
Qi-Yu
QY
Wang
Mei-Xiang
MX
D000588:Amines / Q000737:chemistry; D000838:Anions / Q000737:chemistry*; D019817:Benzoic Acid / Q000737:chemistry; D047250:Calixarenes / Q000737:chemistry*; D047248:Crown Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D004952:Esters / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D014227:Triazines / Q000737:chemistry*
D000588:Amines; D000838:Anions; D047248:Crown Compounds; D004952:Esters; D014227:Triazines; D047250:Calixarenes; D019817:Benzoic Acid; D005459:Fluorides