6-Chloro-1-phenylindoline-2,3-dione: absolute structure, non-linear optical and charge-transport properties

Abstract

In the title compound, C14H8ClNO2, the dihedral angle between the isatin moiety (r.m.s. deviation = 0.014 Å) and the phenyl ring is 51.8 (1)°. All molecules have the same `frozen chiral' conformation in the non-centrosymmetric P212121 space group. A polycrystalline sample of the title compound exhibits a considerable second-order non-linear optical effect (frequency doubling of 1064 nm light to output 532 nm light). In the crystal, molecules are linked by C—H...O hydrogen bonds, generating chains along the [100] direction. Based on a DFT calculation, [100] proves to be the most favourable direction for charge transport and the title crystal could be used as a hole-transport material because of its high hole mobility.

Keywords

• crystal structure
• absolute structure
• isatin derivatives
• frozen chiral conformation
• SHG effect
• charge-transport property