Nanofibril Materials for Highly Sensitive and Selective Sensing of Amines

Abstract

where A and A′ are independently chosen from N—R1, N—R2, and O such that both A and A′ are not O, and R1 through R10 are amine binding moieties, solubility enhancing groups, or hydrogen such that at least one of R1 through R10 is an amine binding moiety. This perylene compound can be formed into well-defined nanofibers. Upon deposition onto a substrate, the entangled nanofibers form a meshlike, highly porous film, which enables expedient diffusion of gaseous analyte molecules within the film matrix, leading to a milliseconds response for vapor sensing.

What is claimed is: 
     
         1 . An amine sensor assembly comprising a porous film of entangled nanofibers on a substrate, the nanofibers having a stacked nanofiber structure including a 3,4,9,10-tetracarboxyl perylene compound having the formula I: 
       
         
           
           
               
               
           
         
         where A and A′ are independently chosen from N—R1, N—R2, and O such that both A and A′ are not O, and R1 through R10 are independently selected from the group consisting of amine binding moieties, solubility enhancing groups, and hydrogen such that at least one of R1 through R10 is an amine binding moiety. 
       
     
     
         2 . The amine sensor assembly of  claim 1 , wherein A is N—R1 and A′ is O. 
     
     
         3 . The amine sensor assembly of  claim 2 , wherein R1 is a C1 to C13 alkyl. 
     
     
         4 . The amine sensor assembly of  claim 2 , wherein R1 is hexylheptyl, pentylhexyl, or butylpentyl. 
     
     
         5 . The amine sensor assembly of  claim 1 , wherein A is N—R1 and A′ is N—R2. 
     
     
         6 . The amine sensor assembly of  claim 5 , wherein at least one of R1 and R2 is a C1 to C13 alkyl. 
     
     
         7 . The amine sensor assembly of  claim 5 , wherein at least one of R1 and R2 is selected from the group consisting of hexylheptyl, pentylhexyl, butylpentyl, COOH, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclododecyl. 
     
     
         8 . The amine sensor assembly of  claim 5 , wherein one or two of R3 through R10 is COOH. 
     
     
         9 . The amine sensor assembly of  claim 1 , wherein R4 and R5 collectively form maleic anhydride. 
     
     
         10 . The amine sensor assembly of  claim 1 , wherein the nanofibers have a diameter from about 10 nm to about 1000 nm. 
     
     
         11 . The amine sensor assembly of  claim 10 , wherein the nanofibers have a diameter from about 10 nm to about 50 nm 
     
     
         12 . The amine sensor assembly of  claim 1 , wherein the amine-binding moiety includes an oxygen moiety or an acid. 
     
     
         13 . The amine sensor assembly of  claim 12 , wherein amine-binding moiety is an anhydride. 
     
     
         14 . The amine sensor assembly of  claim 12 , wherein the amine-binding moiety is a carboxylic acid. 
     
     
         15 . The amine sensor assembly of  claim 1 , wherein R3-R10 contains at least one amine-binding moiety or solubility enhancing group. 
     
     
         16 . The amine sensor assembly of  claim 1 , wherein A is N—R1 and A′ is O and R1 is a branched alkyl or wherein A is N—R1 and A′ is N—R2 and the second amine-binding moiety is an anhydride or carboxylic acid and the solubility enhancing group is a branched alkyl. 
     
     
         17 . A method of detecting amines in a fluid, comprising:
 a) exposing the fluorescent sensor compound of  claim 1  to a fluid sample; and   b) displaying a fluorescence change upon exposure of the nanofiber sensor compound to the fluid sample.