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Synthesis And Reactions Of Di(Thiophen-2-Yl)Alkane Diones: Cyclocondensation, Teki̇n Artunç, Abdullah Menzek

Turkish Journal of Chemistry

Known 1,6-di(thiophen-2-yl)hexane-1,6-dione (2) and novel 1,7-di(thiophen-2-yl)heptane-1,7-dione (4) were obtained from the reactions of thiophene with the corresponding diacyl chlorides. Furthermore, compounds with furan and pyrrole units in place of thiophene units in compound 2 were obtained in the same way. Bromination of 2 and 4 gave bromides regioselectively. The reaction of each of the compounds 2 and 4 in HOAc medium yielded cyclocondensation products. In total, four known and eleven novel compounds were synthesized.

Crystal Engineering Of Asymmetric And Pyrene Fused Annulenes For Use In Organic Electronic Materials, Garrett Fregoso

Theses and Dissertations--Chemistry

Since the development of TiPS Pentacene, the use of trialkylsilylethynyl groups has become a commonly utilized moiety for stabilizing, solubilizing, and directing crystal packing of acenes and acene-like compounds, leading to the development of a well-defined series of trends that aid in the prediction of crystal packing for the development of organic semiconducting materials. While these trends have been extensively studied in mainly symmetric linear systems, it is important to determine how, if at all, asymmetry of the aromatic core affects these well-defined trends. This constitutes the basis of Chapter 2, which explores the crystal engineering and physical properties of …

Unsymmetrical Zinc Phthalocyanines Containing Thiophene And Amine Groups As Donor For Bulk Heterojunction Solar Cells, Gülnur Keser Karaoğlan, Öznur Dülger Kutlu, Ahmet Altindal

Turkish Journal of Chemistry

Photovoltaic technology is an alternative resource for renewable and sustainable energy and low costs organic photovoltaic devices such as bulk-heterojunction (BHJ) solar cells, which are selective candidates for the effective conversion of solar energy into electricity. Asymmetric phthalocyanines containing electron acceptor and donor groups create high photovoltaic conversion efficiency in dye sensitized solar cells. In this study, a new unsymmetrical zinc phthalocyanine was designed and synthesized including thiophene and amine groups at peripherally positions for BHJ solar cell. The structure of the targeted compound (4) was characterized comprehensively by FT-IR, UV-Vis, 1H-NMR, and MALDI-TOF MS spectroscopies. The potential of this …

An Anthracene Based Fluorescent Probe For The Selective And Sensitive Detection Of Chromium (Iii) Ions In An Aqueous Medium And Its Practical Application, Erman Karakuş

Turkish Journal of Chemistry

An anthracene based fluorescent probe, integrated with thiophene moiety, exhibited selective and sensitive detection of chromium (III) ions over other metal ions. Its synthesis was achieved by simple mixing of two commercially available compounds, 2-aminoanthracene, and 2-thiophenecarboxaldehyde, in onestep without the needed complex purification process. The probe molecule (ANT-Th) offered exceptional features such as "turn-on" fluorescence response, low detection limit (0.4 μM), and fast response time (< 1 min) via C$=$N bond hydrolysis. Also, a simple test paper system was developed for the rapid detection of chromium (III) ions with the naked eye.

Extrapolating The Excitation Energy Of Polythiophene From Thiophene Oligomers, Jacob H. Wat, Graham Griffin

DePaul Discoveries

Organic semiconductors are used solar cells and as energy transferring materials. They can be separated into oligomers and polymers. In current computational studies oligomers are used to extrapolate the behavior of polymers. To do so many oligomers are created to extrapolate trends based on oligomer size. In this study a computer program was created to enable the quick and efficient production of oligomers ranging from 1 to 166 monomer units in length. The code was used to create thiophene oligomers. Through applying a linear fit, W. Khun fit and a polynomial fit excitation energy was predicted to be 2.001±0.002 eV, …

Investigation Of The Effects Of Hydrogen Bonding On The Enantiomeric Excess Of Pig Liver Esterase Hydrolysis Products, Matthew Hasler

Honors Theses

Pig Liver Esterase (PLE) is an effective enzyme used in the Masterson Research Group due to its ability to hydrolyze only one ester in a malonic diester. PLE is employed for creating chiral molecules for the synthesis of unnatural amino acid precursors. Previous research in the group found that malonic half esters with hydrogen bonding capable substrates yielded varying degrees of enantiomeric excess, and non-hydrogen bonding substrates yielded racemic mixtures.1,2 The compounds synthesized contained substrates consisting of thiophene rings in the second and third position, and these molecules act as a control for the other research done in the group. …

Molecular Design, Characterization, And Implementation Of Organic Semiconducting Oligothiophenes, Benjamin Cherniawski

Doctoral Dissertations

This work describes new self-assembly strategies and realizes new directions for rational side chain design in organic semiconductors. I examined the synthesis and structure property relations of monomers and dimers of a benchmark organic semiconductor system using a variety of linear alkyl side chains. I observed critical onsets for packing trends based on alkyl side chain length in both monomers and dimers. Monomer systems exhibited a pronounced even-odd effect manifesting directly from side chain length. In the dimer systems, I observed spontaneous bimolecular crystal formation with PC₆₁BM which undergoes an order-to-disorder transition at small side chain lengths. Combining …

Synthesis And Characterization Of New Thiophene--Benzimidazole-Based Electrochromes, Emi̇ne Gül Cansu Ergün

Turkish Journal of Chemistry

In the present study, two new donor--acceptor--donor-type molecules were synthesized and the electro-optical properties of the resulting monomers and their corresponding polymers were investigated. Thiophene was selected as the donor unit and cycloheptyl- and cyclooctyl- substituted benzimidazoles were used as the acceptor units. The synthesized monomers and their electrochemically obtained polymers were characterized using cyclic voltammetry and UV-Vis spectrometry. The optical band gap values of the polymers were 1.62 eV and the polymer films changed color to gray upon oxidation, while they were brick red in their neutral states. Moreover, changing the ring size on the acceptor group from seven …

Organometallic Materials: Ferroceno[C]Thiophenes And 1,2-Bisthienylmetallocenes, Surya R. Banks

Theses and Dissertations--Chemistry

Development of synthetic routes toward two general organometallic frameworks was undertaken. The first project involved synthetic attempts of substituted and unsubstituted ferroceno[c]thiophene while the second one was the synthesis of 1,2-dithienylmetallocenes. The long-term goal of this work is to lay the foundations for study of electronic, electrochromic, redox, and optical properties of thiophene-based materials integrated with organometallic systems such as ferrocene, ruthenocene and cymantrene. The synthetic pathway for the target molecule in the first project involved converting 1,2-bis(hydroxymethyl)ferrocene to 1,2-bis(thiouroniummethyl)ferrocene with thiourea under acidic conditions. Refluxing the salt in base followed by acidification resulted in 1,2-bis(mercaptomethyl)ferrocene, which is …

Novel Thiophene Supported N,N'-Chelating Ligands And Their Main Group Compounds, Jacquelyn T. Price

Electronic Thesis and Dissertation Repository

Main group chemistry has advanced from studying fundamental curiosities, including low oxidation state, low-valent, p-block elements to tailoring these unique, reactive species for specific functional applications. This thesis examines the structure, bonding and reactivity of select group 13, 14 and 15 elements supported by N,N'-chelating ligands decorated with either thiophene, benzo[1,2-b:5,6-b']dithiophene or bis(2,5-dimethylthienyl)ethene substituents and allowing for subsequent reactivity and photophysical properties to be determined.

The synthesis of a new diamino ligand containing a thiophene ring in the backbone was used to support a 7-membered phosphenium cation. The 1:1 stoichiometric reaction between the amine:chlorophosphine was dependant on the substitution …

Effects Of Thiophene Units On Substituted Benzothiadiazole And Benzodithiophene Copolymers For Photovoltaic Applications, Ping Ding, Yingping Zou, Cheng-Che Chu, Dequan Xiao, Chain-Shu Hsu

Chemistry and Chemical Engineering Faculty Publications

Two conjugated copolymers, P1 and P2, comprising of benzodithiophene and 5, 6-dioctyloxy-benzothiadiazole (DOBT) derivatives with/without thiophene unit, were synthesized via Stille cross-coupling polymerization reaction. These copolymers are promising for the applications in BHJ solar cells due to their good solubilities， proper thermal stability and moderate hole mobility as well as low bandgap. The photovoltaic properties of the copolymers were investigated based on the blend of the different polymer/PC71BM weight ratio under AM1.5G illumination, 100 mW/cm2. The device with ITO/PEDOT:PSS/P2: PC71BM (1:2, w/w)/Ca/Al gave relatively better photovoltaic performance, with a power conversion efficiency of 1.55%.

Cyanoacetamide Derivatives As Synthons In Heterocyclic Synthesis, Ahmed Ali Fadda, Samir Bondock, Ramy Rabie, Hassan Ali Etman

Turkish Journal of Chemistry

This review presents a systematic and comprehensive survey of the methods of preparation and the chemical reactivity of cyanoacetamide derivatives. These compounds are important intermediates for the synthesis of a variety of otherwise difficult to obtain synthetically useful and novel heterocyclic systems.

Syntheseses [Sic] And Evaluation Of Porphyrin Derivatives For Applications In Medicine And In Material Science, Erhong Hao

LSU Doctoral Dissertations

Chapter 1 presents a concise introduction to porphyrins, especially on the synthesis of meso-tetraphenylporphyrins, which were synthesized during the course of my research and were used for further purposes in the following chapters. Chapter 2 describes the synthesis of a series of cobaltacarborane-porphyrin conjugates for the boron neutron capture therapy (BNCT) of tumors. Using an efficient and high yield ring-opening reaction, N-substituted porphyrins were also synthesized. The spectroscopic and structural properties of these compounds are presented. These high percentage boron and amphiphilic compounds are promising boron delivery agents for BNCT (prelimary cellular studies using some of these compounds have been …

Acid-Base Equilibria Of Some N-Substituted Thiophene-2-Carboxamidoximes In Non-Aqueous Media, Nedi̇me Dürüst, Yaşar Dürüst, İlknur Meri̇ç

Turkish Journal of Chemistry

The protonation constants of the amino nitrogens of some N-substituted thiophene-2-carboxamidoximes have been determined in acetic acid by means of potentiometric titration with perchloric acid. pK_{a} values of the title compounds were interpreted on the basis of structural effects due to the substituents and the main skeleton.

The Influnce Of Conjugated Π Bond In Promoter Molecule On The Direct Electrochemical Reaction Of Cytochrome C, Xiaogang Qu, Tianhong Lu, Shaojun Dong

Journal of Electrochemistry

The promoter effect of thiophene with only one-functional group on the directelectrochemical reaction of cytochrome c was compared with that of tetrahydrothiophene in this report.It was found that thiophene is a good promoter.But tetrahydrothiophene could not facilitate the directelectrochemistry of cytochrome c although this compound is very similar to thiophene in str uctureexcept for conjugated π bond.This demonstrated that the conjugated π bond in thiophene plays animportant role for the acceleration of the direct electrochemistry of cytochrome c.