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Title: New Approach for the Synthesis of Mono- , A1/A2- Di – andPentahydroxy Functionalized Pillar[5]arenes : Synthesis,
Authors: Abdirahman Abbi Mohamud 
Supervisor: Dr. Talal F. Al-Azemi
Keywords: Pentahydroxy Functionalized Pillar[5]arenes : Synthesis,
Issue Date: 2018
Publisher:  Kuwait university - college of graduate studies
Abstract: Pillar[n]arenes are recently discovered versatile class of macrocyclic compounds which find many interesting applications in supramolecular chemistry such as encapsulation, molecular recognition and host-guest interactions. In this study, the well-defined mono- , A1/A2- di – and pentahydroxy functionalized pilla[5]arenes have been synthesized by preparing pillar[5]arene(s)- bearing varying degree of benzyl groups first and consequent removal of the benzyl group(s) using catalytic hydrogenation. These synthesized compounds are then characterized by NMR, MS spectral analysis and X-ray single crystal diffraction technique. Host-guest complexation between a Mono-hydroxy-pillar[5]arene with long-chain alkyl alcohol guests was studied and found that encapsulation characteristics of the pillar[5]arene was affected by the presence of hydroxyl groups. The investigation on novel planar-chiral Monohydroxy-functionalized pillar[5]arenes, which are amenable to a wide variety of chemical modifications, has also been carried out by synthesizing bulky cyclohexynyl substituted pillar[5]arene having one attached Mosher group. Chiral resolution was performed using derivatization with Mosher’s acid chloride (S)-(+)-α-Methoxy-α-trifluoromethylphenylacetyl chloride ((S)-(+)-MTPA-Cl), and the absolute configurations of the this obtained MTPA ester–functionalized pillar[5]arenes were determined by single-crystal X-ray diffraction.
Appears in Programs:0420 Chemistry (Ph.D.)

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