Synthesis and Optical Characterization of a Novel Benzofuran-Based Molecule: 3-Amino-2-Pinacolone Benzofuran

Abstract

In the present study, a novel benzofuran-based compound, 3-amino-2-pinacolone benzofuran (APBF), was synthesized in high yield via the aldol condensation of 2-hydroxybenzonitrile with 1-chloropinacolone in the presence of potassium carbonate and acetonitrile. The structure of APBF was confirmed by FTIR and 1H, 13C-NMR spectroscopic analyses, which clearly defined its spectral characteristics. The UV–Vis absorption properties of APBF were comprehensively investigated to elucidate its photophysical behavior. Intense absorption bands were observed corresponding to π→π* transitions within the conjugated benzofuran framework, while the red-shifted bands were attributed to n→π* transitions arising from the carbonyl and amino functional groups. The APBF molecule exhibited excellent optical transparency in the higher wavelength region. Some optical dispersion parameters, including the single-oscillator energy, dispersion energy, oscillator strength, and oscillator wavelength were determined from the dispersion analysis. The optical band gap was found to be 3.311 eV indicating potential suitability of APBF for electro-optical applications. The relatively low Urbach energy (0.035 eV) indicated a well-ordered molecular structure with minimal defect-induced disorder confirming the excellent optical quality of the present molecule.

Keywords

• Benzofuran
• Uv–vis spectroscopy
• Optical properties
• Dispersion parameters

Benzofuran Temelli Yeni Bir Molekülün Sentezi ve Optik Karakterizasyonu: 3-Amino-2-Pinakolon Benzofuran

Abstract

Bu çalışmada, yeni bir benzofuran yapılı bileşik olan 3-amino-2-pinakolon benzofuran (APBF) bileşiği, potasyum karbonat ve asetonitril varlığında 2-hidroksibenzonitril ile 1-kloropinakolonun aldol kondenzasyonu yoluyla yüksek verimle sentezlendi. FTIR ile 1H ve 13C-NMR spektroskopik analizleri, APBF bileşiğinin yapısını doğrulamış ve karakteristik spektral özelliklerini açık bir şekilde ortaya koymuştur. UV–Vis absorpsiyon özellikleri ayrıntılı olarak incelenmiş ve bileşiğin fotofiziksel davranışı aydınlatılmıştır. Gözlenen güçlü absorpsiyon bantlarının, konjuge benzofuran iskeletindeki π→π* geçişlerinden kaynaklandığı; kırmızı dalga boyuna kaymış bantların ise karbonil ve amino fonksiyonel gruplarına ait n→π* geçişlerinden kaynaklandığı belirlenmiştir. APBF molekülü, yüksek dalga boyu bölgesinde mükemmel optik geçirgenlik sergilemiştir. Dağılım analizlerinden osilatör enerjisi, dağılım enerjisi, osilatör şiddeti ve osilatör dalga boyu gibi optik dağılım parametreleri belirlenmiştir. Optik bant aralığı 3.311 eV olarak bulunmuş olup, APBF molekülünün elektro-optik uygulamalar için potansiyel bir aday olabileceğini göstermektedir. Ayrıca, nispeten düşük Urbach enerjisi (0.035 eV), kusur kaynaklı düzensizliklerin oldukça az olduğu, iyi düzenlenmiş bir moleküler yapıya işaret etmektedir ve mevcut molekülün yüksek optik kalitesini doğrulamaktadır.

Keywords

• Benzofuran
• UV–Vis spektroskopisi
• Optik özellikler
• Dağılım parametreleri.

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