Synthesis and Absorption Properties of Trisubstituted Hetarylazo Indole Dyes

Yıl 2020, Cilt: 15 Sayı: 1, 63 - 72, 31.05.2020

Mehmet Ulutürk , Tahir Tilki

https://doi.org/10.29233/sdufeffd.649535

Öz

In this study, as a result of azo coupling of diazonium salts prepared with various aromatic amines with 2-(4-methylphenyl)-1H-indole and 2-(4-chlorophenyl)-1H-indole compounds, a series of new hetarylazo indole dyes were synthesized. N-substituted indole derivatives were synthesized by alkylation of the prepared dyes with the isopropyl alcohol from the N-position by Mitsunobu reaction. The chemical structures of the synthesized compounds were determined by NMR, FT-IR, UV-vis, mass spectrometry and elemental analysis. In order to determine the photophysical properties of the dyes obtained, visible region absorption spectra were examined in solvents of different polarity. In addition, the behavior of acid and base addition on absorption maxima were examined in detail.

Anahtar Kelimeler

Indole derivatives, Azo compounds, Mitsunobu alkylation, Solvent effect

Destekleyen Kurum

SDU-BAP

Proje Numarası

3497-D1-13

Teşekkür

The authors are grateful to SDU-BAP (Project No: 3497-D1-13) for their financial support.

Trisübstitüe Hetarilazo İndol Boyalarının Sentezi ve Absorpsiyon Özelliklerinin İncelenmesi

Öz

Bu çalışmada, çeşitli aromatik aminler ile hazırlanan diazonyum tuzlarının, 2-(4-metilfenil)-1H-indol ve 2-(4-klorfenil)-1H-indol bileşikleri ile azo kenetlenmesi sonucu, bir dizi yeni hetarilazo indol boyası sentezlendi. Hazırlanan boyarmaddelerin, Mitsunobu reaksiyonu ile N-pozisyonundan izopropil alkol ile alkillenmesi sonucu N-sübstitue indol türevlerinin sentezi gerçekleştirildi. Sentezlenen bileşiklerin kimyasal yapıları, NMR, FT-IR, UV-vis, kütle spektrometresi ve elementel analiz ile aydınlatıldı. Elde edilen boyarmaddelerin fotofiziksel özelliklerini belirlemek için, farklı polariteye sahip çözücüler içerisinde görünür bölge absorpsiyon spektrumları incelendi. Ek olarak, asit ve baz ilavesinin absorpsiyon maksimumları üzerine etkileri ayrıntılı olarak incelendi.

Anahtar Kelimeler

İndol türevleri, Azo bileşikleri, Mitsunobu alkilasyonu, Çözücü etkisi

Proje Numarası

3497-D1-13

Kaynakça

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