TY - JOUR
T1 - Nonlinear optical organic co-crystals of merocyanine dyes and phenolic derivatives with short hydrogen bonds
AU - Bosshard, Christian
AU - Pan, Feng
AU - WONG, Ricky M S
AU - Manetta, Sabine
AU - Spreiter, Rolf
AU - Cai, Chengzhi
AU - Günter, Peter
AU - Gramlich, Volker
N1 - Funding Information:
We thank the Swiss National Science Foundation for financial support, J. Hajfler for his expert sample preparation, and Marcel Ehrensperger for the differential scanning calorimetry determination.
PY - 1999/7/1
Y1 - 1999/7/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0033447785&partnerID=8YFLogxK
U2 - 10.1016/S0301-0104(99)00134-2
DO - 10.1016/S0301-0104(99)00134-2
M3 - Article
AN - SCOPUS:0033447785
SN - 0301-0104
VL - 245
SP - 377
EP - 394
JO - Chemical Physics
JF - Chemical Physics
IS - 1-3
ER -