Frictionless molecular rotary motors

• US 8,715,635 B2
• Filed: 02/06/2008
• Issued: 05/06/2014
• Est. Priority Date: 02/06/2007
• Status: Expired due to Fees

• Current Assignee: TECHNION RESEARCH AND DEVELOPMENT FOUNDATION, LTD. (Technion-Israel Institute Of Technology)
• Original Assignee: TECHNION RESEARCH AND DEVELOPMENT FOUNDATION, LTD. (Technion-Israel Institute Of Technology)
• Inventors: Keinan, Ehud
• Primary Examiner(s): ROGERS, JAMES WILLIAM
• Application Number:
  US12/526,046
• Publication Number:
  US 20100016610A1
• Time in Patent Office: 2,281 Days
• Field of Search: None
• US Class Current: 424/78.17
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings

Abstract

A rotaxane consisting of a cucurbituril and an uncharged guest molecule, having low or null affinity therebetween is provided as well as processes for providing the same. Various uses as energy converters (“frictionless” molecular motors), biochips and biosensors using the same are also provided.

Claims

1. A rotaxane comprising a host molecule and a guest molecule, said host molecule being a cucurbit[n]uril (CB[n]), and said guest molecule having the general Formula I:

U—

B₁-L₁-[A]_m-L₂-B₂—

Y 

 

Formula I

wherein;

n is an integer that ranges from 5 to 20;

B₁ and B₂ are each independently an uncharged stopper moiety;

L₁ and L₂ are each independently an uncharged linking moiety or absent;

[A]_m is a linear and rigid threading moiety having a neutral net charge at a pH that ranges from 6-8;

whereas A is selected from the group consisting of a 1,2-ethyn-di-yl, substituted or unsubstituted cyclobuta-1,3-diene-1,3-di-yl, substituted or unsubstituted pentalene-2,5-di-yl, substituted or unsubstituted pyrene-2,7-di-yl, C-substituted or unsubstituted pyridine-2,5-di-yl, C—

substituted or unsubstituted pyrimidine-2,5-di-yl, C-substituted or unsubstituted pyrazine-3,6-di-yl and 1,2,4,5-tetrazine-3,6-diyl, and

m is an integer that ranges from 1 to 50; and

U and Y are each independently selected from the group consisting of an anchoring group, an effector moiety, a detectible moiety, a biomolecule, or absent.

2. The rotaxane of claim 1, wherein n ranges from 5 to 8.

3. The rotaxane of claim 1, wherein A is a 1,2-ethyn-di-yl.

4. The rotaxane of claim 1, wherein said stopper moiety is selected from the group consisting of a branched alkyl moiety, a branched cycloalkyl moiety, a branched heteroalicyclic moiety, a branched polyaryl moiety, a branched polyheteroaryl moiety, an adamantly moiety, a branched organophosphorous, a branched organoboron, a branched organosilicon and a branched carboranes.

5. The rotaxane of claim 1, wherein said linking moiety is selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, heteroalicyclic, aryl, heteroaryl, ether, thioether, amide, ester, carbamate, thioamide, thiocarbamate, imine, aza, organophosphorous, organoboron and organosilicon.

6. The rotaxane of claim 1, wherein said effector moiety is selected from the group consisting of a charged moiety, a metal ion complex moiety, a magnetic moiety and a light absorbing moiety.

7. The rotaxane of claim 1, wherein said cucurbit[n]uril further comprises at least one functionality attached thereto selected from the group consisting of an anchoring group, an effector moiety, a detectible moiety and a biomolecule.