The Pentastar was adopted as Chrysler's new corporate logo in the middle of the 1963 model year. There is a 1963 TSB giving dealers the part numbers and installation instructions for the passenger-side Pentastar emblem on '63 vehicles that didn't come from the factory that way. Early '63 keys were the same as '62 keys: Aluminum with the Forward Look logo on them. Round head for trunk, trapezoid for ignition and doors. Later '63 and early '64 keys had the same shape, but were now made out of plated brass and had the pentastar and "CHRYSLER Corporation" stamped into the trapezoidal head:
The key you describe, with the shank coming out of one of the flat sides of the pentagon and the ringhole added onto one of the pentagon's points, was a mid-'64 introduction and lasted through '67. For '68, the pentagon was turned 180° to make the common Y152 blank (with the shank out of one of the pentagon's points and the ringhole added to one of the flats). That blank lasted through to the end of single-bit keys in '89 (trucks and vans maybe a little later).