C.C1C(Br)=C(Br)[NH:4]C=1C(O)=O.N([O-])=O.[Na+].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[N+:23]([O-:26])([OH:25])=[O:24]>O>[N+:23]([O-:26])([O-:25])=[O:24].[C:17]1([N+:16]#[N:4])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
A carbon black with a surface area of 58 m2 /g and a DBPA of 46 ml/100 g was used. A suspension of 50 g of this carbon black was prepared by stirring it into 450 g of water. A solution of 0.85 g of NaNO2 in 4 g of cold water was slowly added to a solution of 0.94 g of aniline and 1.98 g of concentrated nitric acid in 5 g of water that was cooled in an ice bath. Benzenediazonium nitrate was formed. After 15 minutes of stirring, the mixture was added to the stirring carbon black suspension. Bubbles were released. When the bubbling had stopped, the product was collected by filtration, washed twice with water and dried in an oven at 125° C. The carbon black product had attached phenyl groups.
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