Thiophene-derivatized pentiptycenes were synthesized and characterized by NMR and UV-Vis spectroscopy. Aggregation behavior of thiophene-derivatized pentiptycenes was monitored by the measurement of fluorescence. Fluorescence intensities for the thiophene-derivatized pentiptycenes and thiophene-derivatized pentiptycenes aggregates were compared. There is no shift in the maximum of the emission wavelength. In the range of water fraction between 20% and 40%, the emission intensity of thiophene-derivatized pentiptycene aggregates remains almost identical. Fluorescence efficiency incresaed by about 5 times higher when the thiophene-derivatized pentiptycenes forms the aggregates in solution.