{"title":"Color center creation by dipole stacking in crystals of 2-methoxy-5-nitroaniline","authors":"Jonathan Filley","doi":"10.1107/S2056989024008739","DOIUrl":null,"url":null,"abstract":"<div><div>The title compound 2-methoxy-5-nitroaniline forms orange–red crystals and displays shifts in light absorption to longer wavelengths in solution as the concentration increases. Molecular face-to-face stacking with dipoles oriented antiparallel creates a color center, which is compared to certain inorganic semiconductors.</div></div><div><div>This work describes the X-ray structure of orange–red crystals of 2-methoxy-5-nitroaniline, C<sub>7</sub>H<sub>8</sub>N<sub>2</sub>O<sub>3</sub>. The compound displays concentration-dependent UV-Vis spectra, which is attributed to dipole-induced aggregation, and light absorption arising from an intermolecular charge-transfer process that decreases in energy as the degree of aggregation increases. The crystals display π-stacking where the dipole moments align antiparallel. Stacked molecules interact with the next stack <em>via</em> hydrogen bonds, which is a state of maximum aggregation. Light absorption by charge transfer can be compared to colored inorganic semiconductors such as orange–red CdS, with a band gap of 2.0–2.5 eV.</div></div>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"80 10","pages":"Pages 1003-1005"},"PeriodicalIF":0.5000,"publicationDate":"2024-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11451495/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Crystallographica Section E: Crystallographic Communications","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2056989024001968","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CRYSTALLOGRAPHY","Score":null,"Total":0}
引用次数: 0
Abstract
The title compound 2-methoxy-5-nitroaniline forms orange–red crystals and displays shifts in light absorption to longer wavelengths in solution as the concentration increases. Molecular face-to-face stacking with dipoles oriented antiparallel creates a color center, which is compared to certain inorganic semiconductors.
This work describes the X-ray structure of orange–red crystals of 2-methoxy-5-nitroaniline, C7H8N2O3. The compound displays concentration-dependent UV-Vis spectra, which is attributed to dipole-induced aggregation, and light absorption arising from an intermolecular charge-transfer process that decreases in energy as the degree of aggregation increases. The crystals display π-stacking where the dipole moments align antiparallel. Stacked molecules interact with the next stack via hydrogen bonds, which is a state of maximum aggregation. Light absorption by charge transfer can be compared to colored inorganic semiconductors such as orange–red CdS, with a band gap of 2.0–2.5 eV.
这项研究描述了 2-甲氧基-5-硝基苯胺（C7H8N2O3）橙红色晶体的 X 射线结构。该化合物显示出与浓度相关的紫外-可见光谱，这归因于偶极子诱导的聚集，以及分子间电荷转移过程产生的光吸收，该过程的能量随着聚集程度的增加而降低。晶体呈现π堆积，偶极矩反平行排列。堆叠的分子结构通过氢键与下一个堆叠相互影响，这是一种最大聚集状态。电荷转移的光吸收可与带隙为 2.0-2.5 eV 的彩色无机半导体（如橙红色的 CdS）相比较。
期刊介绍：
Acta Crystallographica Section E: Crystallographic Communications is the IUCr''s open-access structural communications journal. It provides a fast, simple and easily accessible publication mechanism for crystal structure determinations of inorganic, metal-organic and organic compounds. The electronic submission, validation, refereeing and publication facilities of the journal ensure rapid and high-quality publication of fully validated structures. The primary article category is Research Communications; these are peer-reviewed articles describing one or more structure determinations with appropriate discussion of the science.
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