Synthesis and Properties of Carboxylic Acid Functionalized Near IR Absorbing Thiophene Fused BODIPY Compounds

Year 2025, Volume: 7 Issue: 1, 92 - 102

Yusuf Çakmak

Abstract

Boron dipyrromethene dyes are one of the most important types of compounds in various fields such as chemical indicators, biological labelling, photodynamic therapy, and solar cells. One of the important derivatives of these dyes are the thiophene-fused BODIPY structures. These structures impart special features such as near IR absorption, heavy atom free photosensitization and compact structure. Although having important aspects, these derivatives of dyes suffer from low synthetic yields. In a few decades various derivatives of fused BODIPY structures were published. However, still more studies are needed to increase the number of these dyes in order to exploit more features and increase the synthetic yields. In the current work, two near-infrared absorbing thiophene fused Bodipy compounds, named CTFBOD1-2, were designed, synthesized and characterized using various techniques. Both compounds were substituted with meso-4-carboxyphenyl units since we have investigated their potential for dye-sensitized solar cell structures. And as electron donor structures, 4-methoxyphenyl and hexylthiophene units were attached to form a donor-acceptor structure. Photophysical and cyclic voltammetry characterizations were also accomplished. In the hexyl-thiophene attached structure (CTFBOD2) we have observed more bathochromic shift in both absorption and emission probably due to the stronger electron pull ability of the thiophene unit. With this structure up to 775 nm absorption is observed, and it is highly important to reach this window with compact structures for solar harvesting. We have observed that the compounds could have been investigated as building blocks in various fields such as dye-sensitized solar cell concept as a photosensitizer.

Keywords

BODIPY, Chemosensors, Dyes, Dye sensitized solar cell, Photodynamic therapy

Supporting Institution

The author thanks TUBITAK (Project No: 216Z015) for financial support

Project Number

216Z015

Yakın-Kızılötesinde Absorplayan, Karboksilik Asit ile Fonksiyonlandırılmış Tiyofen Kaynaşık BODIPY Bileşiklerinin Sentezi ve Özellikleri

Abstract

Bor dipirrometen boyaları, kimyasal indikatörler, biyolojik etiketleme, fotodinamik terapi ve güneş pilleri gibi çeşitli alanlarda en önemli bileşik türlerinden biridir. Bu boyaların önemli türevlerinden biri de tiyofen ile kaynaşmış BODIPY yapılarıdır. Bu yapılar, yakın IR absorpsiyonu, ağır atomsuz ışığa duyarlılık ve kompakt yapı gibi özel özellikler kazandırır. Oldukça önemli özellikler barındırmalarına rağmen, bu boyar madde türevleri düşük sentetik verimlere sahip olabilmektedirler. Birkaç on yıl içinde, kaynaşmış BODIPY yapılarının çeşitli türevleri yayınlandı. Bununla birlikte, daha fazla özellikten yararlanmak ve sentetik verimi artırmak için bu boyaların sayısını artırmak için daha fazla çalışmaya ihtiyaç vardır. Bu çalışmada, CTFBOD1-2 olarak adlandırılan iki adet yakın kızılötesi bölgeden absorplama yapabilen tiyofen ile kaynaşmış Bodipy bileşikleri tasarlanmış, sentezlenmiş ve çeşitli teknikler kullanılarak karakterize edilmiştir. Her iki bileşik de mezo-4-karboksifenil birimleri ile türevlendirilmiştir, çünkü boya duyarlı güneş pili yapıları için potansiyel bileşik olma durumları vardır. Ve elektron verici yapıları olarak, bir donör-alıcı yapı oluşturmak için 4-metoksifenil ve hegziltiyofen birimleri de ayrıca sübstitüe edilmiştir. Fotofiziksel ve döngüsel voltametri karakterizasyonları da gerçekleştirilmiştir. Hegzil-tiyofen bağlı yapıda (CTFBOD2), muhtemelen tiyofen biriminin daha güçlü elektron itme kabiliyetine bağlı olarak hem absorpsiyon hem de emisyonda daha fazla batokromik kayma gözlemlenmiştir. Bu yapı ile 775 nm'ye kadar absorplama gözlenebilmekte ve güneş hasadı için kompakt yapılarla bu pencereye ulaşmak son derece önemlidir. Bileşiklerin, ışığa duyarlılaştırıcı olarak boya duyarlı güneş pili konsepti gibi çeşitli alanlarda yapı taşları olarak kullanılabileceği gözlemlenmiştir.

Keywords

BODIPY, Boyar maddeler, Boya duyarlı güneş pilleri, Fotodinamik terapi, Kimyasal sensörler

Supporting Institution

TÜBİTAK

Project Number

216Z015

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