Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 10, Pages 3268-3273Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo100273n
Keywords
-
Categories
Funding
- ministry of Education, Culture, Sports, Science and Technology, Japan [KIBAN C-20550120, WAKATE B-21750140]
Ask authors/readers for more resources
A series of pillar[5]arene derivatives with alkyl groups of different length were synthesized. The new alkyl-substituted pillar[5]arene derivatives 1,4-bis(ethoxy)pillar[S]arene (C2), 1,4-bis(propoxy)pillar[5]arene (C3), 1,4-bis(butoxy)pillar[5]arene (C4), 1,4-bis(pentyloxy)pillar[5]arene (C5), 1,4-bis(hexyloxy)pillar[5]arene (C6), and 1,4-bis(dodecanoxy)pillar[5]arene (C12) were obtained by Lewis acid-catalyzed condensation of dialkoxybenzene monomers with para formaldehyde. The conformational characteristics of the pillar[5]arene derivatives were investigated by dynamic (1)H NMR measurements. When the alkyl substituents were bulkier than methyl groups, the rotation of phenolic units in the pillar[5]arenes was suppressed and their conformation was immobilized. As their length increased, the alkyl substituents packed at the upper and lower rims and thus lowered the conformational freedom of the pillar[5]arenes.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available