Nucleophilic reactions between mercapto-substituted amphiphiles and carbosilane dendrimers bearing (chloromethyl)silyl groups on their terminal branches gave, in high yields, amphiphilic dendrimers with hydrophobic carbosilane cores and alcohol, dimethylamino, or sodium sulfonate amphiphilic groups at the periphery. The negatively charged, sulfonate-terminated dendrimers were soluble in water, as were positively charged poly(ammonium) salts prepared from the dimethylamino-terminated derivatives. These new amphiphilic dendrimers were characterized by spectroscopic and mass spectrometric techniques. Preliminary studies of the aqueous solution behavior of the second generation, sulfonate-terminated dendrimer demonstrated its ability to enhance the solubility of lipophilic allyl-substituted benzene derivatives, a characteristic property of micelles.