Porous diacetylene particles, synthesis method thereof

Abstract

Provided are a radial porous diacetylene particle, which is synthesized by ion-bonding a diacetylene-containing dicarboxylic acid or diamine monomer represented by Formula 1 above with a diamine or dicarboxylic acid monomer represented by Formula 2 above, and a method of manufacturing the same.

1 . A radial porous diacetylene particle, which is synthesized by ion-bonding a diacetylene-containing dicarboxylic acid or diamine monomer represented by Formula 1 below with a diamine or dicarboxylic acid monomer represented by Formula 2 below:
   G-(A) x -C≡C—C≡C—(B) y -G   [Formula 1]
   wherein A and B are each independently selected from a substituted or unsubstituted alkyl group of two or more carbon atoms, an ethylene oxide group, an amide group and an ester group, G is selected from COOH and NH 2 , and x and y are each independently an integer of 1 to 20,
   Q-(D) m -Z-(E) n -Q   [Formula 2]
 
   wherein Z is selected from a substituted or unsubstituted alkyl group of one or more carbon atoms, a benzene group, a cycloalkyl group, a pyridine group, a pyrimidine group and a naphthalene group, D and E are each independently selected from a substituted or unsubstituted alkyl group of one or more carbon atoms, a benzene group, a cycloalkyl group, a pyridine group, a pyrimidine group and a naphthalene group, D, E and Z are different from each other, Q is selected from COOH and NH 2 , m and n are each independently an integer of 0 to 20, and G of Formula 1 above is different from Q of Formula 2 above.   
     
     
         2 . The radial porous diacetylene particle according to  claim 1 , wherein the diamine or dicarboxylic acid monomer represented by Formula 2 above is represented by Formula 3 below:
   Q-(H 2 C) m -C 6 H 4 -(CH 2 ) n -Q   [Formula 3]
   wherein Q is selected from COOH and NH 2 , and m and n are each independently an integer of 1 to 10.   
     
     
         3 . The radial porous diacetylene particle according to  claim 1 , wherein the radial porous diacetylene particle has optical characteristics of color transition and fluorescence-emitting. 
     
     
         4 . The radial porous diacetylene particle according to  claim 1 , wherein the radial porous diacetylene particle has a particle size of 50 nm˜50 μm and a pore size of 1 nm˜1 μm. 
     
     
         5 . A method of manufacturing a radial porous diacetylene particle, comprising the steps of:
 (a) respectively dissolving a diacetylene-containing dicarboxylic acid or diamine monomer represented by Formula 1 below and a diamine or dicarboxylic acid monomer represented by Formula 2 below in a solvent to prepare a solution including the diacetylene-containing dicarboxylic acid or diamine monomer and a solution including the diamine or dicarboxylic acid monomer:
   G-(A) x -C≡C—C≡C—(B) y -G   [Formula 1]
 
   wherein A and B are each independently selected from a substituted or unsubstituted alkyl group of two or more carbon atoms, an ethylene oxide group, an amide group and an ester group, G is selected from COOH and NH 2 , and x and y are each independently an integer of 1 to 20,
   Q-(D) m -Z-(E) n -Q   [Formula 2]
 
   wherein Z is selected from a substituted or unsubstituted alkyl group of one or more carbon atoms, a benzene group, a cycloalkyl group, a pyridine group, a pyrimidine group and a naphthalene group, D and E are each independently selected from a substituted or unsubstituted alkyl group of one or more carbon atoms, a benzene group, a cycloalkyl group, a pyridine group, a pyrimidine group and a naphthalene group, D, E and Z are different from each other, Q is selected from COOH and NH 2 , m and n are each independently an integer of 0 to 20, and G of Formula 1 above is different from Q of Formula 2 above;   (b) ultrasonically treating each of the solutions;   (c) maintaining each of the ultrasonically-treated solutions at room temperature; and   (d) mixing the solution including the diacetylene-containing dicarboxylic acid or diamine monomer represented by Formula 1 above with the solution including the diamine or dicarboxylic acid monomer represented by Formula 2 above to form a radial porous diacetylene particle and then growing the radial porous diacetylene particle.   
     
     
         6 . The method according to  claim 5 , wherein the solvent is at least one selected from the group consisting of tetrahydrofuran (THF), chloroform, toluene, ethanol, isopropanol, and n-hexane. 
     
     
         7 . The method according to  claim 5 , wherein each of the solution including the diacetylene-containing dicarboxylic acid or diamine monomer represented by Formula 1 above and the solution including the diamine or dicarboxylic acid monomer represented by Formula 2 above has a concentration of 10 mM˜50 mM. 
     
     
         8 . The method according to  claim 5 , wherein each of the solution including the diacetylene-containing dicarboxylic acid or diamine monomer represented by Formula 1 above and the solution including the diamine or dicarboxylic acid monomer represented by Formula 2 above has a concentration of 10 mM˜20 mM. 
     
     
         9 . The method according to  claim 5 , wherein the solution including the diacetylene-containing dicarboxylic acid or diamine monomer represented by Formula 1 above and the solution including the diamine or dicarboxylic acid monomer represented by Formula 2 above are maintained at a room temperature of 5˜30° C. for 10 minutes˜1 hour during a mixing process. 
     
     
         10 . The method according to  claim 5 , wherein the solution including the diacetylene-containing dicarboxylic acid or diamine monomer represented by Formula 1 above and the solution including the diamine or dicarboxylic acid monomer represented by Formula 2 above are maintained at a room temperature of 10˜25° C. for 10 minutes˜1 hour during the process of mixing the solution. 
     
     
         11 . The method according to  claim 5 , wherein the solution including the diacetylene-containing dicarboxylic acid or diamine monomer represented by Formula 1 above and the solution including the diamine or dicarboxylic acid monomer represented by Formula 2 above are mixed in a volume ratio of 1:0.2˜5. 
     
     
         12 . The method according to  claim 5 , wherein the ultrasonic treatment is carried out for 30 minutes by a power of 5˜20 W.