Column setting to accept custom date

I wanted to know if there is a way to add a custom date to both tif and pdf
files that you can display in windows explorer and use to sort.

I scan much of my information. Previously used TIF images but not use PDF.
Unfortunately, much of the information gets entered on a date after what I'm
scanning. For instance I might scan a phone bill in Feb that was from the
prior December.

When I look under Microsoft Office Document Imaging you can view properties
and enter "custom information" about that scan but I don't see how you can
sort windows explorer but the custom date.

Any ideas? When I'm in windows explorer I see "column setting" but they
don't match with the custom information" I added to the TIF file.