Method for introducing functional material into organic nanotube

Abstract

The objective is to easily introduce a desired functional substance into organic nanotubes under milder conditions such as ambient temperature and ambient pressure. The method comprises the steps of allowing a surface active organic compound comprising hydrophobic hydrocarbon groups and hydrophilic groups to self aggregate in liquid phase to form organic nanotubes having an internal cavity size of at least 5 nm (step 1), freeze drying the organic nanotubes (step 2), dissolving or dispersing a desired functional substance in a solvent (step 3) and dispersing said freeze dried organic nanotubes in the solvent or the dispersion at or below the gel-liquid crystal phase transition temperature of said surface active organic compound (step 4). The organic nanotubes formed can be used in a variety of applications depending on the properties of the functional substance.

1 - 5 . (canceled)  
     
     
         6 . An organic nanotube having an internal cavity size of at least 5 nm formed by self aggregating a surface active organic compound in liquid phase, wherein a functional substance is introduced into the internal cavity of the organic nanotubes, said surface active organic compound contains a hydrophobic hydrocarbon chain and at least one type of hydrophilic group selected from the group comprising saccharide chains, peptide chains and metal salts, and the hydrocarbon chain and the hydrophilic group are bonded directly or through an amide linkage, arylene group or arylene-oxy group.  
     
     
         7 . The organic nanotube as in  claim 6 , wherein the functional substance is introduced into the internal cavity of the organic nanotubes by a method comprising the steps of freeze drying the organic nanotubes, dissolving or dispersing the desired functional substance in a solvent and dispersing said freeze dried organic nanotubes in the solvent or the dispersion at or below the gel-liquid crystal phase transition temperature of said surface active organic compound.  
     
     
         8 . The organic nanotube as in  claim 6  wherein said hydrophobic hydrocarbon chain is a hydrocarbon chain containing about 6 to 50 carbon atoms.  
     
     
         9 . The organic nanotube as in  claim 7  wherein said hydrophobic hydrocarbon chain is a hydrocarbon chain containing about 6 to 50 carbon atoms.  
     
     
         10 . The organic nanotube as in  claim 6  wherein said surface active organic compound is any one of (a) to (d) shown below: 
 (a) An O-glycoside type glycolipid having a structure shown by the general formula                          whereinG represents a saccharide group and R represents a hydrocarbon group containing 6 to 25 carbon atoms;    (b) An asymmetric double head type lipid represented by the general formula R′—NHCO—(CH 2 )n-COOH, wherein R′ represents an aldopyranose radical from which the terminal reducing hydroxyl group is excluded, and n represents 6 to 20;    (c) An N-glycoside type glycolipid represented by the general formula G′-NHCO—R″ wherein G′ represents a saccharide radical from which a hemiacetal hydroxyl group bonded to the anomer carbon atom in the saccharide is excluded, and R″ represents an unsaturated hydrocarbon group containing 10 to 39 carbon atoms;    (d) A compound comprising a transition metal and a peptide lipid represented by the general formula R′″CO(NHCH 2 CO) m OH, wherein R′″ represents a hydrocarbon group containing 6 to 18 carbon atoms, and m represents an integer of 1 to 3.    
     
     
         11 . The organic nanotube as in  claim 7  wherein said surface active organic compound is any one of (a) to (d) shown below: 
 (a) An O-glycoside type glycolipid having a structure shown by the general formula                          whereinG represents a saccharide group and R represents a hydrocarbon group containing 6 to 25 carbon atoms;    (b) An asymmetric double head type lipid represented by the general formula R′—NHCO—(CH 2 )n-COOH, wherein R′ represents an aldopyranose radical from which the terminal reducing hydroxyl group is excluded, and n represents 6 to 20;    (c) An N-glycoside type glycolipid represented by the general formula G′-NHCO—R″ wherein G′ represents a saccharide radical from which a hemiacetal hydroxyl group bonded to the anomer carbon atom in the saccharide is excluded, and R″ represents an unsaturated hydrocarbon group containing 10 to 39 carbon atoms;    (d) A compound comprising a transition metal and a peptide lipid represented by the general formula R′″CO(NHCH 2 CO) m OH, wherein R′″ represents a hydrocarbon group containing 6 to 18 carbon atoms, and m represents an integer of 1 to 3.    
     
     
         12 . The organic nanotube as in  claim 8  wherein said surface active organic compound is any one of (a) to (d) shown below: 
 (a) An O-glycoside type glycolipid having a structure shown by the general formula                          whereinG represents a saccharide group and R represents a hydrocarbon group containing 6 to 25 carbon atoms;    (b) An asymmetric double head type lipid represented by the general formula R′—NHCO—(CH 2 )n-COOH, wherein R′ represents an aldopyranose radical from which the terminal reducing hydroxyl group is excluded, and n represents 6 to 20;    (c) An N-glycoside type glycolipid represented by the general formula G′-NHCO—R″ wherein G′ represents a saccharide radical from which a hemiacetal hydroxyl group bonded to the anomer carbon atom in the saccharide is excluded, and R″ represents an unsaturated hydrocarbon group containing 10 to 39 carbon atoms;    (d) A compound comprising a transition metal and a peptide lipid represented by the general formula R′″CO(NHCH 2 CO) m OH, wherein R′″ represents a hydrocarbon group containing 6 to 18 carbon atoms, and m represents an integer of 1 to 3.    
     
     
         13 . The organic nanotube as in any  claim 6  wherein the solvent used for self aggregating the surface active organic compound in liquid phase is water, a saline solution or a pH buffer solution and the solvent used for introducing the functional substance into the internal cavity of the organic nanotubes is water or an organic solvent.  
     
     
         14 . The organic nanotube as in  claim 6  wherein the step of dissolving or dispersing the desired functional substance is conducted under atmospheric pressure and at ambient temperature.  
     
     
         15 . The organic nanotube as in  claim 6  wherein the freeze drying is conducted at −70° C. or lower, 20 Pa or lower and for at least 24 hours.  
     
     
         16 . A method for introducing a functional substance into organic nanotubes in a solvent or in a dispersion comprising the steps of freeze drying an organic nanotubes having an internal cavity size of at least 5 nm formed by allowing a surface active organic compound to self aggregate in liquid phase, and dispersing said freeze dried organic nanotubes in the solvent or the dispersion at or below the gel-liquid crystal phase transition temperature of said surface active organic compound, wherein said surface active organic compound contains a hydrophobic hydrocarbon chain and at least one type of hydrophilic group selected from the group comprising saccharide chains, peptide chains and metal salts, and the hydrocarbon chain and the hydrophilic group are bonded directly or through an amide linkage, arylene group or arylene-oxy group.  
     
     
         17 . The method as in  claim 16  wherein said hydrophobic hydrocarbon chain is a hydrocarbon chain containing about 6 to 50 carbon atoms.  
     
     
         18 . The method as in  claim 16  wherein said surface active organic compound is any one of (a) to (d) shown below: 
 (a) An O-glycoside type glycolipid having a structure shown by the general formula                          wherein G represents a saccharide group and R represents a hydrocarbon group containing 6 to 25 carbon atoms;    (b) An asymmetric double head type lipid represented by the general formula R′—NHCO—(CH 2 )n-COOH, wherein R′ represents an aldopyranose radical from which the terminal reducing hydroxyl group is excluded, and n represents 6 to 20;    (c) An N-glycoside type glycolipid represented by the general formula G′-NHCO—R″, wherein G′ represents a saccharide radical from which a hemiacetal hydroxyl group bonded to the anomer carbon atom in the saccharide is excluded, and R″ represents an unsaturated hydrocarbon group containing 10 to 39 carbon atoms;    (d) A compound comprising a transition metal and a peptide lipid represented by the general formula R′″CO(NHCH 2 CO) m OH, wherein R′″ represents a hydrocarbon group containing 6 to 18 carbon atoms, and m represents an integer of 1 to 3.    
     
     
         19 . The method as in  claim 17  wherein said surface active organic compound is any one of (a) to (d) shown below: 
 (a) An O-glycoside type glycolipid having a structure shown by the general formula                          wherein G represents a saccharide group and R represents a hydrocarbon group containing 6 to 25 carbon atoms;    (b) An asymmetric double head type lipid represented by the general formula R′—NHCO—(CH 2 )n-COOH, wherein R′ represents an aldopyranose radical from which the terminal reducing hydroxyl group is excluded, and n represents 6 to 20;    (c) An N-glycoside type glycolipid represented by the general formula G′-NHCO—R″, wherein G′ represents a saccharide radical from which a hemiacetal hydroxyl group bonded to the anomer carbon atom in the saccharide is excluded, and R″ represents an unsaturated hydrocarbon group containing 10 to 39 carbon atoms;    (d) A compound comprising a transition metal and a peptide lipid represented by the general formula R′″CO(NHCH 2 CO) m OH, wherein R′″ represents a hydrocarbon group containing 6 to 18 carbon atoms, and m represents an integer of 1 to 3.    
     
     
         20 . The method as in  claim 16  wherein the solvent used for self aggregating the surface active organic compound in liquid phase is water, a saline solution or a pH buffer solution and the solvent used for introducing the functional substance into the internal cavity of the organic nanotubes is water or an organic solvent.  
     
     
         21 . The method as in  claim 17  wherein the solvent used for self aggregating the surface active organic compound in liquid phase is water, a saline solution or a pH buffer solution and the solvent used for introducing the functional substance into the internal cavity of the organic nanotubes is water or an organic solvent.  
     
     
         22 . The method as in  claim 18  wherein the solvent used for self aggregating the surface active organic compound in liquid phase is water, a saline solution or a pH buffer solution and the solvent used for introducing the functional substance into the internal cavity of the organic nanotubes is water or an organic solvent.