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NMR spectroscopic investigation of benzothiazolylacetonitrile azo dyes : CR7 substitution effect and semiempirical study
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- Alsoghier, H. M. (author)
- South Valley Univ, Fac Sci, Chem Dept, Qena 83523, Egypt.;Univ Lisbon, Ctr Quim Estrutural, Inst Super Tecn, Av Rovisco Pais 1, P-1049001 Lisbon, Portugal.
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- Abdellah, M. (author)
- Uppsala universitet,Institutionen för kemi - Ångström,South Valley Univ, Fac Sci, Chem Dept, Qena 83523, Egypt.
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- Rageh, H. M. (author)
- South Valley Univ, Fac Sci, Chem Dept, Qena 83523, Egypt.
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- South Valley Univ, Fac Sci, Chem Dept, Qena 83523, Egypt;Univ Lisbon, Ctr Quim Estrutural, Inst Super Tecn, Av Rovisco Pais 1, P-1049001 Lisbon, Portugal. Institutionen för kemi - Ångström (creator_code:org_t)
- Elsevier, 2021
- 2021
- English.
- In: RESULTS IN CHEMISTRY. - : Elsevier. - 2211-7156. ; 3
- Journal article (peer-reviewed)
Abstract
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- Ebead et al. had reported in the synthesis and the UV-Visible solvatochromism combined with semiempirical calculations to study the tautomerism of 1,3-benzothiazol-2-ylacetonitrile azo dyes [1]. In this study, 1,3-ben zothiazol-2-ylacetonitrile azo dyes (1-6) have been resynthesized, one and two dimensional H-1 and C-13 NMR, as well as absorption and emission spectra, were collected and interpreted. The obtained results were used to clarify the tautomerization phenomenon of these dyes. Predominantly, these dyes exist in Z-hydrazone form reinforced through intramolecular hydrogen bonding in deuterated chloroform. Substituents (R) in carbon7 (CR7) are the key player of the changes in H-1 and C-13 NMR chemical shifts, also in the absorption and emission wavelengths of benzothiazole azo dyes. Also, the relative photoluminescence quantum yields (PL QY) of these dyes (1-6) were estimated and related to the nature of substituents. Finally, PM6 semiempirical calculations were employed to confirm the preferred geometric structure and experimental NMR, absorption, and emission results.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- Benzothiazole azo dyes
- H-1 and C-13 NMR
- Azo -hydrazone tautomerism
- CR7 in chemistry
- UV-Visible
- Fluorescence spectroscopic properties and quantum yield
- Intramolecular hydrogen bond
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- ref (subject category)
- art (subject category)
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- Alsoghier, H. M.
- Abdellah, M.
- Rageh, H. M.
- Salman, H. M. A.
- Selim, M. A.
- Santos, M. A.
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- Ibrahim, S. A.
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