The Legal Theory Bookworm recommends Robotica: Speech Rights and Artificial Intelligence by Ronald K. L. Collins & David M. Skover. Here is a description:
In every era of communications technology - whether print, radio, television, or Internet - some form of government censorship follows to regulate the medium and its messages. Today we are seeing the phenomenon of 'machine speech' enhanced by the development of sophisticated artificial intelligence. Ronald K. L. Collins and David M. Skover argue that the First Amendment must provide defenses and justifications for covering and protecting robotic expression. It is irrelevant that a robot is not human and cannot have intentions; what matters is that a human experiences robotic speech as meaningful. This is the constitutional recognition of 'intentionless free speech' at the interface of the robot and receiver. Robotica is the first book to develop the legal arguments for these purposes. Aimed at law and communication scholars, lawyers, and free speech activists, this work explores important new problems and solutions at the interface of law and technology.
And from the reviews:
'Collins and Skover have long been among the finest minds focused on free expression in America. In this remarkable book, they now turn insightfully to an incredibly complex and timely issue associated with 'robotic expression': how should the First Amendment handle contests involving regulation of 'robot speech' as artificial intelligence grows rapidly in prominence? This book conveys their deep knowledge - and the knowledge of other noted scholars - of the history, law, and technology that inform the way we should think about this emerging field of constitutional inquiry.' John Palfrey, Head of School at Phillips Academy, Massachusetts; former Executive Director of the Berkman Center for Internet and Society, Harvard University, Massachusetts; and author of Born Digital
'Collins and Skover have produced a wonderfully readable, thorough, and insightful exploration of the intersection of technology and free speech theory, from the beginning of time well into the future. If any current scholarly work of free speech theory survives into the next century, it will undoubtedly be this book.' Martin Redish, Louis and Harriet Ancel Professor of Law and Public Policy, Northwestern University Law School, Illinois, and author of The Adversary First Amendment: Free Expression and the Foundations of American Democracy