D. Herbert Lipson, 88, who transformed Philadelphia Magazine in the 1960s from a business-promoting arm of the Chamber of Commerce to a formidable showcase for investigative journalism and the exemplar of the urban magazine genre, died Monday at the Hospital of the University of Pennsylvania. Recently beset with heart difficulties, Mr. Lipson died following surgery for another ailment, said his son, David, chairman and CEO of Metrocorp, publisher of Philadelphia and Boston Magazines. Born in Philadelphia and raised in Easton, Pa., Mr. Lipson was the son of a newspaper owner, S. Arthur Lipson, who moved to Philadelphia to get into the magazine business, thinking it less hectic than newspapers. Arthur Lipson ultimately would buy Greater Philadelphia Magazine from the chamber of commerce. Mr. Lipson went to work for his father in 1953 at what became Philadelphia Magazine, one year after graduating from Lafayette College. He became the owner in 1968 with partner Ralph Lopatin. Lopatin died in the early 1980s, leaving Mr. Lipson as sole owner. Mr. Lipson married three times and had three children. Most recently, he divided his time between homes in Margate, N.J., and Naples, Fla. In addition to his son and his daughter Sherry Litwer, he is survived by his wife, Carol; another daughter, Debbie Claremon; a sister, seven grandchildren, and one great-grandchild.