Electrochromism with selenophene derivatives

Download
2008
Aydemir, Kadir
A novel selenophene-based monomer; 1,4-di(selenophen-2-yl) benzene (DSB), synthesized via Stille coupling reaction of 1,4 dibromobenzene and tributyl (2-selenophenyl) stannane and corresponding conducting homopolymer (Poly (DSB)) was electrochemically synthesized in the presence of tetrabutylammoniumhexafluorophosphate (TBAPF6) as the supporting electrolyte in dichloromethane. The resulting conducting polymer was characterized by Cyclic Voltammetry (CV), Fourier Transform Infra Red Spectrometry (FTIR) and UltravioletVisible Spectrometry (UV-Vis Spectrometry). Spectroelectrochemistry analysis and kinetic studies of Poly (DSB) revealed * transition ( max) at 340 nm with almost zero percent transmittance ( T%) concurrently with striking and rapid (0.6 s) absorbance change at near infrared region (1250 nm) with 35% percent transmittance, indicating that Poly (DSB) is a very suitable near infrared electrochromic material. Copolymer of selenophene with ethylenedioxythiophene (EDOT) was potentiostatically synthesized. Poly (selenophene-co-EDOT) was characterized by Cyclic Voltammetry, FTIR and UV-Vis Spectrometry. During spectroelectrochemistry studies, * transition ( max) was observed at 555 nm with a switching time of 1.4 s and 39% transmittance. Polaron and bipolaron bands were observed at 851 nm and 1299 nm, respectively. Switching time at 1299 nm was 1.8 s with a percent transmittance of 72. Copolymer of DSB with EDOT (Poly (DSB-co-EDOT)) was synthesized and characterized. max, polaron and bipolaron bands were observed at 457 nm, 696 nm and 1251 nm, respectively. A rapid switching time (0.2 s) with 12% transmittance was observed at 696 nm. At the near infrared region (1251 nm), satisfactory percent transmittance (35%) and a moderate switching time (1.75 s) were observed.

Suggestions

Asymetric synthesis of 1,4-diamine based chiral ligand and organocatalyst and their applications
Ortaylı, Oytun; Tanyeli, Cihangir; Department of Chemistry (2010)
Novel 1,4-chiral diamine ligand possessing a trans-9,10-dihydro-9,10-ethanoanthracene backbone was synthesized. The synthetic plan involves first LiAlH4 reduction of the Diels-Alder adduct obtained by reaction of dimenthyl fumarate and anthracene, which is followed by reacting the corresponding alcohol and subsequent attachment of mesylate and triflate units to get good leaving groups which are available substances for introducing nitrogen units via SN2 type reactions. Consequently, by using dimesyl ester a...
A Low Band Gap Benzimidazole Derivative and Its Copolymer with 3,4-Ethylenedioxythiophene for Electrochemical Studies
Soylemez, Saniye; Hacioglu, Serife O.; Uzun, Sema Demirci; Toppare, Levent Kamil (The Electrochemical Society, 2014-11-7)
A novel monomer; 2-(3-nitrophenyl)-4,7-di(thiophen-2-yl)-1H-benzo[d]imidazole) (BIMN) was used for electrochemical copolymerization with 3,4-ethylenedioxythiophene (EDOT). Polymerization was achieved in acetonitrile (ACN)/dichloromethane (DCM) (1:1, 1:3 and 1:5, molar ratios) solution containing sodium perchlorate (NaClO4) and lithium perchlorate (LiClO4) mixture as the supporting electrolyte on an ITO electrode. The chemical structures of monomer and copolymers were characterized by nuclear magnetic resona...
Electrochromic performance and ion sensitivity of a terthienyl based fluorescent polymer
Atilgan, Nurdan; CİHANER, ATİLLA; Önal, Ahmet Muhtar (Elsevier BV, 2010-04-01)
A novel terthienyl based fluorescent polymer bearing strong electron-withdrawing substituents directly attached to the 3,4-positions of the central thiophene ring was synthesized by electrochemical polymerization of diethyl 2,5-di(3,4-ethylenedioxythiophen-2-yl)thiophene-3,4-dicarboxylate. The corresponding polymer was characterized by cyclic voltammetry, FT-IR and UV-vis spectroscopy. The polymer has a well-defined redox process (E-p,E-1/2 = 0.74 V) and demonstrates a reversible electrochromic behavior; li...
Thiadiazoloquinoxaline and benzodithiophene bearing polymers for electrochromic and organic photovoltaic applications
Hacioglu, Serife O.; Ataoglu, Emre; Hizalan, Gonul; Depci, Tolga; Çırpan, Ali; Toppare, Levent Kamil (Informa UK Limited, 2019-09-02)
Two novel thiadiazoloquinoxaline and benzodithiophene (BDT) bearing copolymers were designed and synthesized. Different BDT units (alkoxy and thiophene substituted) were used as donor materials and the effect of alkoxy and thiophene substitution on the electrochemical, spectroelectrochemical and photovoltaic properties were investigated. Both polymers exhibited low oxidation potentials at around 0.90 V and low optical band gaps at around 1.00 eV due to the insertion of electron poor thiadiazoloquinoxaline u...
Remarkable cooperative action of two zinc centers in the hydrolysis of plasmid DNA
Aka, FN; Akkaya, Mahinur; Akkaya, EU (Elsevier BV, 2001-01-08)
A novel binuclear zinc complex has been synthesized. The complex is highly efficient in the hydrolysis of plasmid DNA at pH 7.5. Furthermore, a comparison to a mononuclear complex reveals a high level of cooperativity between the two metal ion centers.
Citation Formats
K. Aydemir, “Electrochromism with selenophene derivatives,” M.S. - Master of Science, Middle East Technical University, 2008.