Octupolar (C3 and S4) Symmetric Cyclized Indole Derivatives: Syntheses, Structures, and NLO Properties.

Several cyclized indole derivatives have been synthesized, and their structures been determined. The C3-symmetric single-chiral N-phenyltriindole (Tr-Ph3) crystallized in the P1 space group, and the S4-symmetric saddle-like tetraindole (TTr) crystallized in the I4̅ space group. The Tr-Ph3 and TTr crystals exhibit remarkable powder SHG intensities 5 and 11 times that of KH2PO4 (KDP), respectively. TTr is a useful octupolar core to build S4-symmetric molecules and crystals for second-NLO materials.