Table 1. Gelation Properties of the Synthesized Diacetylene Lipids 6–20a.
| no. | Tol | IPA | EtOH | DMSO/H2O (1:1) | DMSO/H2O (1:2) | EtOH/H2O (1:1) | EtOH/H2O (1:2) | H2O |
|---|---|---|---|---|---|---|---|---|
| 6 | G* 20.0 | P | G 20.0 | G 10.0 | G 10.0 | G 10.0 | P | I |
| 7 | P | S | S | G 10.0 | G 10.0 | G 20.0 | G 10.0 | P |
| 8 | S | P | P | G 10.0 | G 10.0 | G 10.0 | P | P |
| 9 | GC 6.7 | P | P | G 6.7 | G 20.0 | G 5.0 | G 20.0 | I |
| 10 | G 10.0 | G 20.0 | G 10.0 | G 10.0 | G 20.0 | G 10.0 | P | I |
| 11 | GT 10.0 | S | S | G 20.0 | G 6.7 | GT 6.7 | G 6.7 | G 10.0 |
| 12 | G 20.0 | G 20.0 | S | G 20.0 | G 20.0 | G 20.0 | G 20.0 | P |
| 13 | G 10.0 | G 10.0 | P | G 10.0 | G 10.0 | G 20.0 | G 10.0 | I |
| 14 | GC 20.0 | P | G 10.0 | G 5.0 | G 6.7 | G 20.0 | P | I |
| 15 | P | P | G 10.0 | G 10.0 | P | G 3.3 | P | I |
| 16 | P | P | P | P | G 5.0 | G 20.0 | G 5.0 | I |
| 17 | P | S | S | P | P | G 10.0 | P | I |
| 18 | G 10.0 | GT* 20.0 | S | G 4.0 | G 5.0 | G 2.5 | GT* 20.0 | P |
| 19 | GC 10.0 | GT* 20.0 | P | G 6.7 | G 10.0 | G* 20.0 | P | I |
| 20 | G 5.0 | G 20.0 | G 20.0 | G 20.0 | I | P | I | I |
All compounds were tested starting from 20 mg/mL. G, stable gel at rt and G* partial gel or unstable gel at 20 mg/mL; the numbers next to “G” are MGCs in mg/mL; P, precipitation; S, soluble; and I, insoluble. All gels were opaque except those labeled. The subscribed letters denote the gel appearances: C, clear or transparent and T, translucent; all compounds were insoluble in hexane, except compound 15, which formed a precipitate.