1. I don't think there's conjugation between the indigo core and the terephthaloyl linker. Try and draw some resonance structures and you'll see for yourself.
2. My opinion is that your polymer has Rf = 1 in EtOAc (travels all the way up); however, it also has very low solubility in it and, as a result, you get a continuous streak from the baseline to the front, with most of your sample resting at the application point. Try running TLC with more dilute samples.