سنتز، بررسی خواص طیف‌سنجی و محاسبات نظریه تابع چگالی تعدادی از رنگزاهای آزوی جدید بر پایه 5-کلرو-8-هیدروکسی کینولین

نوع مقاله : مقاله پژوهشی

نویسندگان

گروه شیمی، دانشکده علوم، واحد لاهیجان، دانشگاه آزاد اسلامی، لاهیجان، گیلان، صندوق پستی: 1616

چکیده

در این پژوهش، دو مشتق کلردار 2-آمینوبنزوتیازول از حلقوی شدن مشتق آنیلین مربوطه در پتاسیم تیوسیانات به کمک اکسایش ملایم با برم در حلال اسید استیک و در دمای اتاق تهیه شدند. در ادامه 2- آمینو بنزوتیازول و هریک از این دو آمین در حضور نیتروزیل اسید سولفوریک دی آزوته شده و با 5-کلرو- 8- هیدروکسی کینولین جفت شده و سه رنگزای هترآریل آزوی مربوطه تهیه شدند. حلال‌پوشی آنها در حلال­های مختلف مورد بررسی قرارگرفت. تغییرات جذبی ترکیبات حاصل در شرایط اسیدی و بازی نیز مورد مطالعه قرار گرفتند. نقطه ایزوبستیک وجود تعادل بین دو ساختار خنثی و آنیونی را نشان داد. بر این اساس ثابت تفکیک اسیدی رنگزاهای حاصل در دمای °C23 -20 در حلال اتانل-آب (20:80) به روش طیف‌سنجی اندازه‌گیری شدند. همچنین، محاسبات نظریه تابع چگالی الکترونی (DFT) به منظور مقایسه انرژی توتومرهای آزو و هیدرازون رنگزاها انجام شدند.

کلیدواژه‌ها

عنوان مقاله [English]

Synthesis, spectroscopic evaluation and density functional theory calculations of some new azo dyes based on 5-chloro-8-hydroxyquinoline

نویسندگان [English]

  • F. Ashouri Mirsadeghi
  • E.O. Moradi Rufchahi
  • S. Zarrabi
Department of Chemistry, Faculty of Science, Lahijan Branch, Islamic Azad University, Lahijan, Iran
چکیده [English]

In this study, two 2-aminobenzothiazole derivatives were prepared by the reaction of appropriate substituted anilines with potassium thiocyanate in acetic acid followed by mild cyclization oxidation reaction with bromine at room temperature. Then, 2-aminobenzothiazole and each of the two synthesized amines were diazotized with nitorsyl sulfuric acid and coupled with 5-chloro-8-hydroxy quinoline to prepare corresponding heteroarylazo dyes. Their solvatochromism was evaluated in different solvents. The effects of acid and base on the absorption maximum wavelengths of the compounds were also studied. From the optical spectra, in each case, the isosbestic points indicate that the two species are in equilibrium. For all of the compounds under investigation, the dependence of the absorbance on the pH value gives sigmoid curves. The acidity constants (pKa) of the dyes were also determined using the spectrophotometric method in an ethanol-water mixture (80:20, v/v) at 20-23°C. Besides, density functional theory (DFT) calculations were carried out in order to compare the energies of proposed azo and hydrazone tautomers of the dyes.

کلیدواژه‌ها [English]

  • : 2-aminobenzothiazole
  • solvatochromism
  • spectroscopic properties
  • azo dyes
  • 8-hydroxyquinoline
  • density functional theory

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