I just recalled that seeing it from a requirements engineeing perspective, the work of Steve Fickas and Martin Feather is of fundamental importance.
I am referring to their classical paper Requirements Monitoring in Dynamic Environments.
I beliieve it is also important to take a look at Requirements-based monitors for real-time systems from Peters and Parnas.
Another research is worth mentioning: Bill Robison is working with monitors for some time, a recent work from him is: Implementing Rule-Based Monitors within a Framework for Continuous Requirements Monitoring.