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5-[(Pyren-9-ylmethyl)amino]isophthalic acid with nitrogen containing heterocycles: stacking, N–H⋯π interactions and photoluminescence
CrystEngComm ( IF 3.1 ) Pub Date : 2021-09-01 , DOI: 10.1039/d1ce01099a Jagajiban Sendh 1 , Munendra Pal Singh 2 , Jubaraj B. Baruah 1
CrystEngComm ( IF 3.1 ) Pub Date : 2021-09-01 , DOI: 10.1039/d1ce01099a Jagajiban Sendh 1 , Munendra Pal Singh 2 , Jubaraj B. Baruah 1
Affiliation
Different synthons, π-stackings and intermolecular N–H⋯π interactions guided by partner molecules in the cocrystals of a pyrene-derived dicarboxylic acid were demonstrated. For such a purpose the self-assemblies of a 1 : 1 solvate of dimethylformamide and 1 : 1 cocrystals with 6-phenyl-1,3,5-triazine-2,4-diamine (PTDA), 4,6-dimethylpyrimidin-2-amine (DMPA) or caffeine as well as a 2 : 1 cocrystal with phenazine (Phen) of 5-[(pyren-9-ylmethyl)amino]isophthalic acid (H2L) were studied. The π-stackings among the pyrene rings in these self-assemblies were compared. Different synthons and stacking patterns in these assemblies were also evaluated. The DMF solvate as well as the PTDA cocrystal of H2L had parallel π-stacks of pyrene rings, each of which were organised in a head-to-tail manner (where the head was the substituted end of pyrene and the tail was the opposite end of this). Both the assemblies had intermolecular N–H⋯π interactions. Phenazine was eclipsed between two isophthalic acid units in the phenazine cocrystal. It had η3-N–H⋯π intramolecular interactions. The assembly of the cocrystal with DMPA had pairs of stacked pyrene units organised in a parallel manner. These units were held together by intermolecular η2-N–H⋯π interactions. The cocrystal of caffeine with H2L was obtained as a trihydrate. In this cocrystal the caffeine molecule was sandwiched between the π-stack of the two pyrene rings located on the top and the bottom side of the caffeine molecule. Self-assembly of a 1 : 1 salt, namely a mono-protonated 4,4′-bipyridinium cation with [HL]−, was also analysed. The 4,4′-bipyridinium salt of the HL anion had the pyrene rings assembled as pairs and were arranged in a head-to-tail arrangement. It lacked intermolecular N–H⋯π interactions. It had unusual pyridine–pyridine R22(6) synthons formed by C–H⋯N hydrogen bonds. Among the cocrystals the caffeine cocrystal was weakly fluorescent with a photoluminescence quantum yield (PLQY) 0.036, whereas the solid sample of the solvate and the other cocrystals as well as the salt of H2L showed negligible emission.
中文翻译:
具有含氮杂环的 5-[(Pyren-9-ylmethyl)amino]isophthalic acid:堆积、N-H⋯π 相互作用和光致发光
在芘衍生的二羧酸的共晶中,由伙伴分子引导的不同合成子、π-堆积和分子间 N-H⋯π 相互作用被证明。为此目的,二甲基甲酰胺的 1:1 溶剂化物和 1:1 与 6-苯基-1,3,5-三嗪-2,4-二胺 (PTDA)、4,6-二甲基嘧啶-2 共晶的自组装研究了-胺(DMPA)或咖啡因以及与吩嗪(Phen)的5-[(芘-9-基甲基)氨基]间苯二甲酸(H 2 L)的2:1共晶。比较了这些自组装体中芘环之间的 π 堆积。还评估了这些组件中不同的合成子和堆叠模式。DMF 溶剂化物以及 H 2的 PTDA 共晶L 具有平行的 π 叠芘环,每个芘环都以头对尾的方式组织(其中头是芘的取代端,尾是芘的另一端)。两个组件都具有分子间 N–H⋯π 相互作用。吩嗪在吩嗪共晶中的两个间苯二甲酸单元之间黯然失色。它具有 η 3 -N–H⋯π 分子内相互作用。共晶与 DMPA 的组装具有以平行方式组织的成对堆叠的芘单元。这些单元通过分子间 η 2 -N–H⋯π 相互作用结合在一起。咖啡因与H 2的共晶L以三水合物形式获得。在这个共晶中,咖啡因分子夹在位于咖啡因分子顶部和底部的两个芘环的 π 堆叠之间。还分析了 1:1 盐(即具有 [HL] -的单质子化 4,4'-联吡啶鎓阳离子)的自组装。HL 阴离子的 4,4'-联吡啶鎓盐具有成对组装的芘环,并以头对尾的方式排列。它缺乏分子间 N–H⋯π 相互作用。它具有由 C–H⋯N 氢键形成的不寻常的吡啶-吡啶 R 2 2 (6) 合成子。在共晶中,咖啡因共晶发出微弱荧光,光致发光量子产率 (PLQY) 为 0.036,而溶剂化物和其他共晶的固体样品以及 H 的盐2 L 显示出可忽略不计的排放。
更新日期:2021-09-20
中文翻译:
具有含氮杂环的 5-[(Pyren-9-ylmethyl)amino]isophthalic acid:堆积、N-H⋯π 相互作用和光致发光
在芘衍生的二羧酸的共晶中,由伙伴分子引导的不同合成子、π-堆积和分子间 N-H⋯π 相互作用被证明。为此目的,二甲基甲酰胺的 1:1 溶剂化物和 1:1 与 6-苯基-1,3,5-三嗪-2,4-二胺 (PTDA)、4,6-二甲基嘧啶-2 共晶的自组装研究了-胺(DMPA)或咖啡因以及与吩嗪(Phen)的5-[(芘-9-基甲基)氨基]间苯二甲酸(H 2 L)的2:1共晶。比较了这些自组装体中芘环之间的 π 堆积。还评估了这些组件中不同的合成子和堆叠模式。DMF 溶剂化物以及 H 2的 PTDA 共晶L 具有平行的 π 叠芘环,每个芘环都以头对尾的方式组织(其中头是芘的取代端,尾是芘的另一端)。两个组件都具有分子间 N–H⋯π 相互作用。吩嗪在吩嗪共晶中的两个间苯二甲酸单元之间黯然失色。它具有 η 3 -N–H⋯π 分子内相互作用。共晶与 DMPA 的组装具有以平行方式组织的成对堆叠的芘单元。这些单元通过分子间 η 2 -N–H⋯π 相互作用结合在一起。咖啡因与H 2的共晶L以三水合物形式获得。在这个共晶中,咖啡因分子夹在位于咖啡因分子顶部和底部的两个芘环的 π 堆叠之间。还分析了 1:1 盐(即具有 [HL] -的单质子化 4,4'-联吡啶鎓阳离子)的自组装。HL 阴离子的 4,4'-联吡啶鎓盐具有成对组装的芘环,并以头对尾的方式排列。它缺乏分子间 N–H⋯π 相互作用。它具有由 C–H⋯N 氢键形成的不寻常的吡啶-吡啶 R 2 2 (6) 合成子。在共晶中,咖啡因共晶发出微弱荧光,光致发光量子产率 (PLQY) 为 0.036,而溶剂化物和其他共晶的固体样品以及 H 的盐2 L 显示出可忽略不计的排放。