Journal
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
Volume 17, Issue 4, Pages 264-282Publisher
WORLD SCI PUBL CO INC
DOI: 10.1142/S1088424613500168
Keywords
discotic liquid crystal; phthalocyanine; fullerene; phthalocyanine-fullerene dyad; homeotropic alignment; organic thin film solar cell
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan [2236012311]
- Grants-in-Aid for Scientific Research [22360123] Funding Source: KAKEN
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In our previous work, we could successfully synthesize the 1:1 phthalocyanine-fullerene (Pc-C-60) dyads, (OFbaC(60))PcCu(OCH3) 2, in very high yields (81 similar to 96%) by using Prato reaction. In this study, we have prepared novel Pc-C-60 dyads, (OFbaC(60)) PcM (M = Co (a), Ni (b), Cu (c), metal free (d)) 3a-3d without the methoxy group. The target Pc-C-60 dyads 3a-3d could be successfully synthesized in good yields also by Prato reaction. It is surprising for us that removal of a very small methoxy group from the big (OFbaC(60))PcCu(OCH3) molecule (2) significantly lowers the cp of (OFbaC(60))PcCu (3c) by about 70 degrees C in comparison with that of 2 having the methoxy group. Very interestingly, each of the novel dyads 3a-3d synthesized here shows perfect homeotropic alignment in the tetragonal columnar phase (Col(tet)). Moreover, it is noteworthy that 3c and 3d show only one Col(tet.o) mesophase having ordered stacking distance with perfect homeotropic alignment. Such simple phase transition can contribute to maintain stable performance in wide temperature range, when they will be applied to organic thin film solar cells.
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