What's the difference between “睡不着” and "没睡着“？
"睡不著" implies that you want to sleep but you cannot, while "沒睡著" just means that you did not fall asleep. So if you say "昨晚我一夜沒睡著" you could mean that you successfully kept yourself awake all night last night, which is apparently different from "昨晚我一夜睡不着".

Actually, although "牙疼死了，一夜沒睡着" is OK, "牙疼死了，一夜睡不著" is better.