The Brookings Institute recently sponsored a series of articles on how new technologies require new approaches to legal regulation in the area of civil liberties. My own contribution was recently posted here: Use Restrictions and the Future of Surveillance Law. You can see the rest of the essays here, by authors including Larry Lessig, Jack Goldsmith, Jamie Boyle, TIm Wu, and Stephen Morse, among others.
The essays were designed to be read by a generalist audience, so they should be more readable than the usual legal academic mumbo-jumbo. Jeffrey Rosen and Benjamin Wittes edited the volume, which I believe will be published eventually as a book.