In this paper, we reported that optically active supramolecular assemblies of an achiral phthalocyanine
derivative, silicon 2,3,9,10,16,17,23,24-octakis(octyloxy)-29H,31H-phthalocyanine dihydroxide (Pc 1), could be
easily achieved through the Langmuir and Langmuir−Schaefer (LS) technique. We have found that the LS film
of Pc 1 showed weak Cotton effect (CE) when it was subjected to the circular dichroism (CD) measurements.
The chirality of the LS film was suggested to be due to the spontaneous symmetry breaking occurred at the
air/water interface. More interestingly, such assemblies connected through the noncovalent bond could be further
converted into covalent bond under heating at 180 °C in a high vacuum for 10 h. UV−vis spectra and FT-IR
have confirmed the polymerization of Pc 1 in the LS film during the heating, which resulted in the formation of
the corresponding phthalocyaninato−polysiloxane (PcPs 2) polymer. Stronger Cotton effect was detected for the
thin solid film of PcPs 2 compared with that of the Pc 1 LS film, suggesting that more efficient exciton coupling
existed between the covalently linked phthalocyanine chromophore in the polymer PcPs 2. The investigation
provided an easy way of constructing optically active polymeric PcPs films exclusively from achiral monomer
unit by the preassembly of monomer through interfacial organization.