Highly thermo- and photostable, near-infrared-absorbing heptamethine cyanine dyes were achieved with the use of fluorine-containing components. In particular, one prepared heptamethine cyanine dye, bearing a tetrakis(pentafluorophenyl)borate as a counter anion and an N-ethyl-2,2,2-trifluoroacetamido group at the meso position, showed not only a high decomposition temperature (T_dt), but also very high photostability toward white LED irradiation.

A direct, concise, and enantioselective synthesis of 2-substituted 4,4,4-trifluorobutane-1,3-diols based on the organocatalytic asymmetric direct aldol reaction of an ethyl hemiacetal of trifluoroacetaldehyde with various aldehydes was examined. A catalytic amount (30 mol %) of commercially available and inexpensive l-prolinamide is quite effective as an organocatalyst for the catalytic in situ generation of gaseous and unstable trifluoroacetaldehyde from its hemiacetal, and a successive asymmetric direct aldol reaction with various aldehydes in dichloromethane at 0 °C, followed by reduction with sodium borohydride, gives 2-substituted 4,4,4-trifluorobutane-1,3-diols in moderate to good yields (31–84 %) with low diastereoselectivities and good to excellent enantioselectivities (64–97 % ee).

The fluorous prolinol methyl ether was prepared through the perfluorohexylethylation of (S)-1-tert-butyl 2-methyl pyrrolidine-1,2-dicarboxylate using commercially available perfluorohexylethyl iodide, methylation, and deprotection in three steps in 19 % overall yield. In the asymmetric Michael addition reaction of nitrostyrene with propanal, the diastereoselectivity (syn/anti=92:8) with the prepared fluorous prolinol methyl ether was much higher than that (syn/anti=87–80:13–20) with nonfluorinated prolinol methyl ethers that have two n-octyl groups or two phenyl groups in place of perfluorohexylethyl groups.