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首页> 外文期刊>Crystal growth & design >Synthesis, Structure, and Topological Studies of Solvates and Salts of a Chiral Zwitterionic Host N-(2-Imidazol-5-yl-1-carboxyethyl)-1,8-naphthalimide
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Synthesis, Structure, and Topological Studies of Solvates and Salts of a Chiral Zwitterionic Host N-(2-Imidazol-5-yl-1-carboxyethyl)-1,8-naphthalimide

机译：手性两性离子主体N-（2-咪唑-5-基-1-羧乙基）-1,8-萘二甲酰亚胺的溶剂化物和盐的合成，结构和拓扑研究

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摘要

A chiral carboxylic acid, (-)-N-(2-imidazol-5-yl-1-carboxyethyl)-1,8-naphthalimide (Hbnap), bearing imide and imidazole functionalities with some structural relevance to tryptophan and histidine amino acids, was designed. Various solvates and salts of Hbnap were synthesized and structurally characterized, namely, Hbnap center dot H2O (1), 4Hbnap center dot MeOH center dot 3H(2)O (2), Hbnap center dot DMSO {DMSO = dimethyl sulfoxide} (3), Hbnap center dot DMF {DMF = N,N'-dimethylformamide} (4), Hbnap center dot DMA {DMA = N,N'-dimethylacetamide} (5), Hbnap center dot 2quinoline (6), Hbnap center dot pyridine (7), bnap center dot Hdbu center dot 2H(2)O {dbu = 1,8-diazabicyclo[5.4.0]undec-7-ene} (8), [H(2)bnap]Br center dot 0.5MeOH (9), [H(2)bnap](I)center dot 0.5MeOH (10), [H(2)bnap](2)SO4 center dot DMF center dot H2O (11), and [H(2)bnap]NO3 (12). Their packing patterns were analyzed in detail, showing that an interplay of hydrogen bonds, aquation, and pi-stacking control the formation of distinct one-, two-, or three-dimensional (1D, 2D, or 3D) supramolecular assemblies. The H-bonded 2D underlying networks of solvates 1-8 were topologically classified revealing three distinct topological types, namely, an undocumented topology in 1 and the 3,4L127 and skl topologies in 2 and 3-8, respectively. In contrast, the [H(2)bnap](+) salts 9-12 show H-bonded underlying networks that are quite distinct not only in the topology (2C1 in 9 and 10, kgd in 11, and lon in 12) but also in the dimensionality that increases from 1D in halide salts 9 and 10 to 2D in sulfate derivative 11 and 3D in nitrate compound 12. Thermogravimetric analysis studies on the removal of DMSO, DMA, and dbu show that packing by the zwitterionic form of the Hbnap host and the formation of salts impede the elimination of solvent in comparison with conventional hydrogen bonded hosts. UV-vis and fluorescence emission studies were also performed showing that different solvates and salts exhibit strong emission bands with distinct maxima in the 428-487 nm region. A significant enhancement of the fluorescence intensity in comparison with the free Hbnap host molecule occurred in all compounds.
机译：一种手性羧酸，（-）-N-（2-咪唑-5-基-1-羧乙基）-1,8-萘二甲酰亚胺（Hbnap），具有酰亚胺和咪唑官能团，与色氨酸和组氨酸氨基酸具有一定的结构相关性，被设计。合成了Hbnap的各种溶剂化物和盐并对其结构进行了表征，即Hbnap中心点H2O（1），4Hbnap中心点MeOH中心点3H（2）O（2），Hbnap中心点DMSO {DMSO =二甲基亚砜}（3） ，Hbnap中心点DMF {DMF = N，N'-二甲基甲酰胺}（4），Hbnap中心点DMA {DMA = N，N'-二甲基乙酰胺}（5），Hbnap中心点2喹啉（6），Hbnap中心点吡啶（ 7），bnap中心点Hdbu中心点2H（2）O {dbu = 1,8-二氮杂双环[5.4.0] undec-7-ene}（8），[H（2）bnap] Br中心点0.5MeOH（ 9），[H（2）bnap]（I）中心点0.5MeOH（10），[H（2）bnap]（2）SO4中心点DMF中心点H2O（11）和[H（2）bnap] NO3（12）。详细分析了它们的堆积模式，表明氢键，水合和pi堆积的相互作用控制了独特的一维，二维或三维（1D，2D或3D）超分子组装的形成。对溶剂化物1-8的H键合2D底层网络进行拓扑分类，揭示了三种不同的拓扑类型，即1中的未记录拓扑以及2和3-8中的3,4L127和skl拓扑。相反，[H（2）bnap]（+）盐9-12显示出H键合的底层网络，这些拓扑不仅在拓扑结构（9和10中的2C1，11中的kgd，12中的lon）方面非常不同。尺寸也从卤化物盐9和10中的1D增加到硫酸盐衍生物11中的2D和硝酸盐化合物12中的3D增大。热重分析对DMSO，DMA和dbu的去除表明，两性离子形式的Hbnap堆积与常规的氢键结合的主体相比，主体和盐的形成阻碍了溶剂的消除。还进行了紫外可见和荧光发射研究，表明不同的溶剂化物和盐在428-487 nm区域显示出强的发射带，并具有明显的最大值。与游离的Hbnap宿主分子相比，荧光强度显着增强。

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