Polymorphism of Merocyanine Dyes Homologues with 1,3-Diethyl-2-thiobarbituric Acid Acceptor and p-Dimethylaminobenzene Donor and Different Polymethine Chains Connecting Them,Crystal Growth & Design

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Polymorphism of Merocyanine Dyes Homologues with 1,3-Diethyl-2-thiobarbituric Acid Acceptor and p-Dimethylaminobenzene Donor and Different Polymethine Chains Connecting Them
Crystal Growth & Design ( IF 3.2 ) Pub Date : 2019-12-19 , DOI: 10.1021/acs.cgd.9b00961
Sergei Rigin ₁ , John Tillotson ₂ , Joseph Perry ₂ , Victor N. Khrustalev _{1,

3} , Georgii Bogdanov ₁ , Tatiana V. Timofeeva ₁

Affiliation

The crystallization from different solvents of homologues of 1,3-diethyl-2-thiobarbituric acid and p-dimethylaminobenzene with different lengths of the polymethine bridge between donor and acceptor groups (TB[n]) produced three pairs of polymorphs with the number of C═C bonds in the chain n = 1, 3, and 5. The homologues with the shortest (one methine unit) π-conjugated bridge were presented by two concomitant (obtained simultaneously) polymorphs. Bond length alternation values calculated using X-ray data and evaluation using NMR data showed that some homologues possesses a very high hyperpolarizability. It was shown that the increase of polarizability is related to the increase in the length of the π-conjugated bridge that was supported by experimental hyper-Rayleigh scattering data. Density functional theory calculations of HOMO/LUMO molecular energy levels indicated that compounds with a longer π-conjugated bridge have a higher thermal stability.

中文翻译：

具有1,3-二乙基-2-硫代巴比妥酸受体和对二甲氨基苯供体的花菁染料同系物的多态性以及连接它们的不同多甲胺链

供体基团和受体基团之间不同长度的聚次甲基桥（TB [ n ]）的1,3-二乙基-2-硫代巴比妥酸和对-二甲基氨基苯的同系物的不同溶剂的结晶产生了三对多晶型，C ═链中的C键n= 1、3和5。具有最短（一个次甲基单位）π共轭桥的同系物由两个伴随（同时获得）的多态性呈现。使用X射线数据计算出的键长交替值以及使用NMR数据进行评估显示，某些同系物具有很高的超极化性。结果表明，极化率的增加与实验超瑞利散射数据所支持的π共轭桥长度的增加有关。HOMO / LUMO分子能级的密度泛函理论计算表明，具有更长π共轭桥的化合物具有更高的热稳定性。

更新日期：2019-12-19

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