Kinolin ve siyanovinilbenzoik asit içeren bileşiklerin duyarlaştırıcı boya olarak güneş hücrelerinde kullanımı
Investigation of compounds containing cyanovinylbenzoic acid and quinoline as sensitizers in solar cells
- Tez No: 1017031
- Danışmanlar: PROF. DR. MEHMET NEBİOĞLU
- Tez Türü: Yüksek Lisans
- Konular: Kimya, Chemistry
- Anahtar Kelimeler: Belirtilmemiş.
- Yıl: 2026
- Dil: Türkçe
- Üniversite: Sakarya Üniversitesi
- Enstitü: Fen Bilimleri Enstitüsü
- Ana Bilim Dalı: Kimya Ana Bilim Dalı
- Bilim Dalı: Organik Kimya Bilim Dalı
- Sayfa Sayısı: Belirtilmemiş.
Özet
Günümüzde fosil yakıtların kullanılmalarıyla ortaya çıkan çevresel problemler ve bu yakıt rezervlerinin azalması insanoğlunu yenilenebilir enerji kaynaklarına yöneltmiştir. Temiz enerji kaynakları arasında en kolay ulaşılabilen ve yaygın olarak kullanılabilen enerji kaynağı güneştir. Güneş enerjisi, bolluk, temizlik, güvenlik ve ekonomik bakımdan yenilenebilir enerji kaynakları içerisinde belki de en önemlisidir. Boya duyarlı güneş hücreleri (BDGH), güneş enerjisini elektriğe dönüştürmede kullanılan ve düşük maliyetli olmalarına rağmen makul enerji dönüşüm verimi sağlayan aygıtlardır. Duyarlaştırıcı olarak kullanılan organik boyaların; çevre dostu olmaları, kolay sentezlenebilmeleri ve molar absorpsiyon katsayılarının büyük oluşu gibi başlıca avantajları bulunmaktadır. Günümüzde ticari güneş panellerin büyük bir çoğunluğu silisyum esaslıdır. Ancak, üretimin maliyetli oluşu ve üretimde toksik kimyasalların kullanılıyor olması silisyum esaslı güneş panelleri için dezavantaj oluşturmaktadır. Buna karşın, boya duyarlı güneş hücreleri düşük maliyet ve düşük ışık yoğunluklarında yüksek performans gibi avantajlara sahiptir. Boya duyarlı güneş hücrelerinde duyarlaştırıcı olarak doğal boyalar, metal kompleks boyalar ve metal içermeyen sentetik boyalar kullanılmaktadır. Genel olarak D−π−A yapısındaki metal içermeyen organik boyalara yardımcı akseptörler (benzotiyadiazol, benzotriazol vb.) bağlanarak D−π−A−π−A yapısında bileşikler elde edilebilmektedir. Bu yapıdaki boyaların kullanıldığı BDGH'ların absorpsiyonun daha uzun dalga boylu bölgeye kaymasıyla daha yüksek fotovoltaik performans gösterdikleri bilinmektedir. Molekül tasarımında kinolin π-köprü görevi görürken, siyanovinilbenzoik asit bağlayıcı grup rolünü üstlenir. Bu yapı sayesinde elektron, uyarılma sonrasında TiO2 yüzeyine etkin biçimde aktarılır. Ayrıca siyanovinil grubunun –CN fonksiyonel grubundaki yüksek elektronegatiflik, HOMO–LUMO aralığını optimize eder ve rekombinasyon kayıplarını azaltır. Bu tez kapsamında metal içermeyen, bağlayıcı grup olarak siyanovinilbenzoik asit ve π-köprüsü olarak kinolin içeren D−π−A−π−A yapısındaki BIM31 ve BIM32 bileşikleri sentezlendi. Boya bileşiklerinin sentezinde başlangıç maddesi olarak ucuz ve kolay temin edilebilen 4-iyodofenol, 4-bromofenol, 4-bromoanilin, o-fenilen diamin, benzene boronik asit gibi basit yapılı bileşikler kullanıldı ve uygun kenetlenme, katılma ve hidroliz tepkimeleri ile uygulandı. Sentezlenen boyaların 1H NMR, 13C NMR ve Sıvı Kromotagrafi Kütle Spektrometresi (LCMS) yöntemleri kullanılarak yapısal karakterizasyonu gerçekleştirildi. Bu boyalar boya duyarlı güneş hücrelerinde duyarlaştırıcı boya olarak kullanıldı. Bu bileşikler yardımcı akseptör olarak benzotiyadiazol ve benzotriazol içermektedir. Tez çalışmasında yardımcı akseptörlerin fotovoltaik performansa etkisi karşılaştırılacaktır. UV-vis ve dönüşümlü voltametri (CV) yöntemleri kullanılarak elektrokimyasal özellikler karakterize edildi ve sentezlenen boyalarla üretilen Boya Duyarlı Güneş Hücreleri'nin akım yoğunluğu-voltaj (J-V) ölçümleri gerçekleştirilerek hücre verimleri hesaplandı. BIM31 ve BIM32 boyalarının CDCA ilavesiyle agregasyon davranışı incelendi, BIM31 boyasının EDV değeri 0,3 mM CDCA ilavesi ile %1,86'dan %3,86'ya yükseldi. BIM32 boyasının EDV değeri ise CDCA ilavesi ile düşmüştür. Bu da BIM32 boyasının agrega olmadığını göstermektedir. EDV değeri yüksek olan BIM32 (%4,93) boyası ile N719 (%7,38) boyasının ortak duyarlaştırması denendi, N719 + BIM32'nin EDV değeri %8,99 olarak bulunmuştur.
Özet (Çeviri)
The increasing environmental problems caused by the intensive use of fossil fuels, together with the gradual depletion of these limited energy resources, have compelled humanity to seek alternative and sustainable energy sources. In this context, renewable energy technologies have attracted significant attention in recent decades. Among renewable energy sources, solar energy stands out as the most abundant, clean, safe, and economically viable option. Due to its unlimited availability and minimal environmental impact, solar energy is considered one of the most promising solutions for meeting the growing global energy demand. Dye-sensitized solar cells (DSSCs) are a class of photovoltaic devices that convert solar energy into electrical energy through a photoelectrochemical process. DSSCs have attracted considerable interest owing to their low production cost, simple fabrication procedures, and relatively high energy conversion efficiencies under both outdoor and indoor light conditions. In particular, their ability to perform efficiently under low light intensities provides a significant advantage over conventional silicon-based solar cells. The sensitizer dye plays a crucial role in DSSCs, as it is responsible for light absorption and electron injection into the semiconductor. Organic dyes used as sensitizers in DSSCs possess several important advantages, including high molar absorption coefficients, structural tunability, environmental friendliness, and ease of synthesis. Compared to metal-complex dyes, metal-free organic dyes offer lower cost, reduced toxicity, and greater flexibility in molecular design. These characteristics make them attractive candidates for next-generation photovoltaic applications. Currently, the majority of commercially available photovoltaic modules are based on crystalline silicon technology. However, the high production cost, energy-intensive manufacturing processes, and the use of toxic or hazardous chemicals represent major drawbacks of silicon-based solar cells. In contrast, DSSCs offer advantages such as lower material costs, shorter energy payback times, and the possibility of using flexible substrates. For this reason, DSSCs have emerged as a promising alternative photovoltaic technology. In DSSC systems, sensitizers can be classified as natural dyes, metal-complex dyes (such as ruthenium-based dyes), and metal-free organic dyes. Among these, metal-free organic dyes with a donor–π–acceptor (D–π–A) molecular architecture have been extensively studied due to their strong light-harvesting capabilities and efficient charge transfer properties. Furthermore, the incorporation of auxiliary acceptor units into the D–π–A framework leads to the formation of more advanced D–π–A–π–A type molecular structures. Auxiliary acceptors such as benzothiadiazole and benzotriazole are commonly used to extend π-conjugation, enhance intramolecular charge transfer, and broaden the absorption spectrum toward longer wavelengths. DSSCs employing dyes with a D–π–A–π–A architecture generally exhibit improved photovoltaic performance as a result of enhanced light absorption in the visible and near-infrared regions. In such molecular designs, the choice of π-bridge and anchoring group is of critical importance. Quinoline-based units are frequently employed as π-bridges due to their rigid aromatic structure and favorable electronic properties. The anchoring group, which ensures strong binding of the dye molecule to the TiO₂ surface, plays a vital role in facilitating efficient electron injection. In this study, cyanovinylbenzoic acid was selected as the anchoring group owing to its strong electron-withdrawing nature and effective binding ability to the TiO₂ semiconductor. The presence of the –CN functional group with high electronegativity contributes to the optimization of the HOMO–LUMO energy gap and suppresses charge recombination processes at the dye–electrolyte interface. As a result, improved charge separation and enhanced photovoltaic performance can be achieved. Within the scope of this thesis, two novel metal-free organic dyes, namely BIM31 and BIM32, possessing a D–π–A–π–A molecular architecture were designed and synthesized. In these dye molecules, quinoline was employed as the π-bridge, while cyanovinylbenzoic acid served as the anchoring group. Benzothiadiazole and benzotriazole units were incorporated as auxiliary acceptors in order to investigate their influence on the optical, electrochemical, and photovoltaic properties of the dyes. The synthesis of the dye molecules was carried out using inexpensive, readily available, and commercially accessible starting materials such as 4-iodophenol, 4-bromophenol, 4-bromoaniline, o-phenylenediamine, and benzene boronic acid. The synthetic routes involved a series of coupling, addition, and hydrolysis reactions conducted under controlled conditions. The use of cost-effective starting materials and straightforward reaction steps highlights the practical feasibility of the proposed dye design. The structural characterization of the synthesized dyes was performed using proton nuclear magnetic resonance (¹H NMR), carbon-13 nuclear magnetic resonance (¹³C NMR), and liquid chromatography–mass spectrometry (LC–MS) techniques. These analyses confirmed the successful synthesis and structural integrity of the target dye molecules. The synthesized dyes were subsequently employed as sensitizers in dye-sensitized solar cells. DSSCs were fabricated using standard procedures, and the influence of the auxiliary acceptor units on device performance was systematically investigated. The optical properties of the dyes were examined using UV–Vis absorption spectroscopy, while their electrochemical properties were evaluated by cyclic voltammetry (CV). These measurements provided valuable information regarding the energy levels and charge transfer behavior of the dye molecules. Photovoltaic performance parameters of the fabricated DSSCs were determined through current density–voltage (J–V) measurements under simulated solar illumination. Power conversion efficiencies (PCE), short-circuit current densities (J_SC), open-circuit voltages (V_OC), and fill factors (FF) were calculated and compared. The aggregation behavior of BIM31 and BIM32 dyes on the TiO₂ surface was investigated using chenodeoxycholic acid (CDCA) as a co-adsorbent. For the BIM31 dye, the addition of 0.3 mM CDCA significantly improved the photovoltaic performance, resulting in an increase in power conversion efficiency from 1.86% to 3.86%. This improvement indicates that CDCA effectively suppresses dye aggregation in the BIM31-based DSSC. In contrast, the power conversion efficiency of the BIM32 dye decreased upon CDCA addition, suggesting that BIM32 does not exhibit significant aggregation behavior on the TiO₂ surface. Furthermore, co-sensitization experiments were conducted to further enhance device performance. The high-efficiency BIM32 dye, exhibiting a power conversion efficiency of 4.93%, was co-sensitized with the widely used standard dye N719, which demonstrated an efficiency of 7.38%. The co-sensitized DSSC based on the N719 + BIM32 dye combination achieved a significantly enhanced power conversion efficiency of 8.99%, demonstrating the effectiveness of the co-sensitization strategy. Overall, the results of this study demonstrate that molecular design strategies involving auxiliary acceptors, appropriate π-bridges, and effective anchoring groups play a crucial role in improving the photovoltaic performance of metal-free organic dyes. The findings contribute to the development of efficient, low-cost, and environmentally friendly sensitizers for dye-sensitized solar cell applications.
Benzer Tezler
- Boya duyarlı güneş hücreleri için farklı akseptör grupları içerenkinolin bileşiklerinin sentezi
Synthesis of quinoline compounds with different acceptor groups for dye-sensitive solar cells
FATİH KAPLAN
- Kinolin ve kinoksalin aminoglioksimlerin sentezi, bunların nikel kompleksleri ve antikanser özelliklerinin incelenmesi
The synthesis of quinolinyl and quinoxaline aminoglyoximes, investigation of their nickel complexes and anticancer properties
NURCAN BAYRAM
- Bazı yeni kinolin türevlerinin sentezi, antimikrobiyal ve DNA giraz inhibitörü etkilerinin araştırılması
Synthesis of new quinoline derivatives and investigation of their antimicrobial and DNA gyrase inhibition effects
ASAF EVRİM EVREN
Yüksek Lisans
Türkçe
2019
Eczacılık ve FarmakolojiAnadolu ÜniversitesiFarmasötik Kimya Ana Bilim Dalı
DOÇ. DR. LEYLA YURTTAŞ
PROF. DR. YUSUF ÖZKAY
- 4-amino-5,7-dikloro-2-metil kinolin, 4-amino-5,8-dikloro-2-metil kinolin moleküllerinin spektroskopik, elektronik ve yapısal özelliklerinin incelenmesi
Investigation of the spectroscopic, electronic and structural properties of 4-amino-5,7-dichloro-2-methyl quinoline,4-amino-5,8-dichloro-2-methyl quinoline molecules
ABDUL HASEEB SHAHID
Yüksek Lisans
Türkçe
2022
Fizik ve Fizik MühendisliğiKırşehir Ahi Evran ÜniversitesiFizik Ana Bilim Dalı
DOÇ. DR. TEVFİK RACİ SERTBAKAN
DOÇ. DR. EMİNE BABUR ŞAŞ
- Tetralon temelli yeni 3-siyano kinolin türevlerinin sentezi, karakterizasyonu ve enzim aktivitelerinin belirlenmesi
Synthesis, characterization and determination of enzyme activities of new tetralone-based 3-cyano quinoline derivatives
İKRANUR YATI
Yüksek Lisans
Türkçe
2025
KimyaTokat Gaziosmanpaşa ÜniversitesiKimya Ana Bilim Dalı
PROF. DR. MUSTAFA CEYLAN