Water-and organic-soluble cucurbituril derivatives, their preparation methods, their separation methods and uses

• US 7,179,908 B2
• Filed: 07/03/2002
• Issued: 02/20/2007
• Est. Priority Date: 07/04/2001
• Status: Expired due to Fees

• Current Assignee: Postech Academy-Industry Foundation
• Original Assignee: Pohang University of Science and Technology Foundation
• Inventors: Kim, Kimoon, Kim, Soo-Young, Oh, Jinho, Kim, Hee-Joon, Zhao, Jianzhang
• Primary Examiner(s): STOCKTON, LAURA LYNNE
• Application Number:
  US10/363,468
• Publication Number:
  US 20030212268A1
• Time in Patent Office: 1,693 Days
• Field of Search: 540/460
• US Class Current: 540/460
• CPC Class Codes: C07D 487/08 Bridged systems
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings

Abstract

Provided are cucurbituril derivatives having the formula (1), their preparation methods and uses:

where X is O, S or NH; R₁ and R₂ are each independently selected from the group consisting of hydrogen, alkyl groups of 1 to 30 carbon atoms, alkenyl groups of 1 to 30 carbon atoms, alkynyl groups of 1 to 30 carbon atoms, alkylthio groups of 1 to 30 carbon atoms, alkylcarboxyl groups of 1 to 30 carbon atoms, hydroxyalkyl groups of 1 to 30 carbon atoms, alkylsilyl groups of 1 to 30 carbon atoms, alkoxy groups of 1 to 30 carbon atoms, haloalkyl groups of 1 to 30 carbon atoms, nitro group, alkylamine groups of 1 to 30 carbon atoms, amine group, aminoalkyl groups of 1 to 30 carbon atoms, unsubstituted cycloalkyl groups of 5 to 30 carbon atoms, cycloalkyl groups of 4 to 30 carbon atoms with hetero atoms, unsubstituted aryl groups of 6 to 30 carbon atoms, and aryl groups of 6 to 30 carbon atoms with hetero atoms; and n and m are independently integers from 4 to 20 and from 1 to 7, respectively. The cucurbituril derivative has enhanced solubility in common solvents, thereby providing wider applications.

Claims

1. A cucurbituril derivative having the formula (1):

2. The cucurbituril derivative according to claim 1, wherein X=O and n is a value of 4 to 10 and m is a value of 1 to 7.

3. The cucurbituril derivative according to claim 1, wherein X=NH or S and n is a value of 4 to 10 and m is a value 1 of 7.

4. A method for preparing a cucurbituril derivative having the formula (1), comprising:

5. The method according to claim 4, wherein in step (a-2), the acid is added in an amount of 3 to 7 moles and the aldehyde compound having the formula (A) is added in an amount of 2 to 20 moles with respect to 1 mole of the compound having the formula (2), and the reaction temperature is in the range of 50 to 150°

C.

6. The method according to claim 4, wherein in step (b-2), the reaction temperature is in the range of 50 to 150°

C.

7. The method according to claim 4, wherein in step (a-2), the acid is selected from the group consisting of hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid and nitric acid and is used as a diluted solution in water or an organic solvent.

8. The method according to claim 4, wherein among reaction products of step (b-2), the cucurbituril derivative with n=5 is produced in a yield of 15 to 50%, the cucurbituril derivative with n=6 is produced in a yield of 2 to 10%, and the cucurbituril derivatives with n=4 and 7 to 10 are produced in a yield of 1 to 5%, respectively.

9. A The method according to claim 4, further comprising separating the cucurbituril derivative having the formula (1) from the cucurbituril derivative mixture by fractional crystallization.

10. The method according to claim 9, wherein at least one solvent selected from the group consisting of water, acetone and acetonitrile is used in the fractional crystallization.