Nonlinear optical organic co-crystals of merocyanine dyes and phenolic derivatives with short hydrogen bonds

Christian Bosshard*, Feng Pan, Ricky M S Wong, Sabine Manetta, Rolf Spreiter, Chengzhi Cai, Peter Günter, Volker Gramlich

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

29 Citations (Scopus)


We investigated the co-crystallization of merocyanine dyes M (M: R-N+C5H4-CH=CH-C6H4O -, M1: R=CH3, M2: R=HO-CH2-CH2-) with phenolic and aniline derivatives and show that the short or very short hydrogen bond between the two phenolic oxygen atoms which lead to a self-assembly of the M dyes and phenol derivatives is the key steering force for the co-crystallization process. The co-crystal formation was studied by melting point determination, by second-harmonic generation using the Kurtz and Perry powder test, and X-ray structural analysis. We present detailed results on the growth, polymorphism, and nonlinear optical properties of co-crystals of derivatives of M1 (M2) and m-nitrophenol (mNP) and co-crystals of M2 and methyl 2,4-dihydroxybenzoate (MDB). Three phases of the co-crystal M2·mNP and three phases of the co-crystal M2·MDB were found. Both M2·MDB(I) and (II) have the same crystal structure (space group symmetry Cc determined by X-ray diffraction), but show different linear and nonlinear optical properties. This unusual property in the co-crystals of M2·MDB(I) and (II) may be caused by a different proton location of the short hydrogen bond (O-H-O) in the aggregation between M2 and MDB which could not be resolved by X-ray diffraction.

Original languageEnglish
Pages (from-to)377-394
Number of pages18
JournalChemical Physics
Issue number1-3
Publication statusPublished - 1 Jul 1999

Scopus Subject Areas

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry


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