Your visa is valid until 23:59:59 on the expiration date. Therefore, from a strictly bureaucratic point of view, you should be allowed to re-enter the Schengen area since you have a valid visa. However, as you say, the immigration officer might have some questions regarding the closeness of the expiry date to your date of entry in the country.
If you want to shed some light on those doubts bring all supporting documents that you think are necessary to explain your situation. These can be in the form of a proof of onward travel - i.e. plane tickets out of the Schengen area on a date prior to the expiry of your visa - or of a proof that you have applied for a visa extension and are likely to get it - say the application submission receipt along with a proof of student status lasting longer than your current visa validity window.
All in all you are the one responsible for bringing the right documentation to support your case. Also I suggest you be honest with the immigration officer and don't try any tricks.