Synthesis and electrochromic properties of oligothiophene derivatives

Yin, Bing; Jiang, Chuanyu; Wang, Yongguang; La, Ming; Liu, Ping; Deng, Wen Jun

doi:10.1016/j.synthmet.2009.11.025

Cited by 32 publications

(12 citation statements)

References 7 publications

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“…Compound 6 [13] was reduced in ethanol by using NaBH 4 to give 3,6-dibromo-4,5-dioctyloxy-1,2-benzenediamine (7) which was protected with acetonide group and oxidized by using manganese oxide to provide 4,7-dibromo-5,6-dioctyloxy-2,2-dimethyl-2H-indene (9). Compound 9 was coupled with tributyl(2-thienyl)stannane [14] in THF by dichlorobis(triphenylphosphine)palladium (II) to give 2-[5,6-dioctyloxy-2,2-dimethyl-7-(2-thienyl)-2H-inden-4-yl]thiophene (10). Compound 10 was brominated in THF by using NBS to give monomer 2-bromo-5-[7-(5-bromo-2-thienyl)-5,6-dioctyloxy-2,2-dimethyl-2H-inden-4-yl]thiophene (11).…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis and photovoltaic properties of alkoxy-benzimidazole containing low band gap polymers

Shim

Kim

et al. 2015

Thin Solid Films

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Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis and photovoltaic properties of alkoxy-benzimidazole containing low band gap polymers

Shim

Kim

et al. 2015

Thin Solid Films

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“…在实际应用的电致变色器件中, 电致变色材料需要与离子传导材料配合使用 [2] , 电致变色材料多为刚性分子链, 离子传导材料多为柔性分子链, 二者之间存在相容性不佳的问题 [7,8] . 如果能够合成这两类材料的共聚物, 则可以完美解决这一问题.…”

Section: 引言unclassified

Synthesis and Characterization of Tetraaniline-Polyethylene Glycol Block and Star-shaped Copolymers

Lu¹,

Yang²

2013

Acta Chim. Sinica

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In this paper, three block or star-shaped tetraaniline-polyethylene glycol copolymers were obtained using a series of methylbenzenesulfonyl chloride homologous compounds as intermediates. To achieve this goal, firstly, tetraaniline was synthesised by 4-aminodiphenyamine through redox reaction in an acidic acetone solution; tetraaniline was then reacted with 4-toluene sulfonyl chloride, 2,5-dimethylbenzenesulfonyl chloride and 2-mesitylenesulfonyl chloride, respectively, to give a series of sulfamide intermediate products with different amounts of capped methyl groups on the benzene ring. These sulfamide intermediate products were oxidized by potassium permanganate, to turn the capped methyl groups equally into carboxyl groups. At last, methoxy polyethylene glycol (PEG) was reacted with these carboxyl groups through esterification reaction to give the tetraaniline-polyethylene glycol copolymers, in which the number of PEG chains was determined by the number of methyl groups on the intermediate products mentioned above. Structure characterization of all related products within the routes, as well as electrical chemical property test of tetraaniline and final products, was carried out using FT-IR, 1 H NMR, UV-Vis, GPC and electrochemical workstation. The results of structure characterization suggested that ideal products were synthesized successfully through designed routes, the cyclic voltammogram and conductivity data suggested that the electrical chemical property of these copolymers was similar with that of tetraaniline, possessing the typical change of oxidation-reduction states. As polyaniline is a typical electrochromism material, whose electrochromism capability is majorly succeeded by tetraaniline, these copolymers could be used in an electrochromism device, in which tetraaniline acts as electrochromism material, while polyethylene glycol acts as ion conducting material. Compared with electrochromism devices formed by polyaniline and polyethylene glycol separately, the ones formed by these copolymers would be much more compatible and processible. Furthermore, the micro structure of an electrochromism device could be formed through copolymers' self-assembly, and the micro phase morphology of the structure could be modified by adjusting the molecular weight of each segment, as well as the number of polyethylene glycol chains.

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“…Among the variety of oligomers used in the synthesis of semi-conducting materials, oligothiophenes have received a high interest, mainly due to the π-electron delocalisation, high polarisability of sulphur atoms and supramolecular organisation coupled with synthetic accessibility [12][13][14]. In particular, alkyl derivatives of oligothiophenes, such as terthiophene and quaterthiophene, constitute an interesting class of electroactive polymers with potential application in organic electronics [15] that can be used as components of active layers for application in electronic devices such as Organic Field Effect Transistors (OFETs) [16,17], photovoltaic cells [18] and electrochromic devices [19]. 3,3'" Dihexyl-2,2':5',2":5",2"'-quaterthiophene (DHQT) is largely investigated for such applications and is usually deposited onto a conductive surface to assemble a device by means of high vacuum evaporation [16,20].…”

Section: Introductionmentioning

confidence: 99%

Copolymerisation as a way to enhance the electrochromic properties of an alkylthiophene oligomer and a pyrrole derivative: copolymer of 3,3′″ dihexyl-2,2′:5′,2″:5″,2′″-quaterthiophene with (R)-(-)-3-(1-pyrrolyl)propyl-N-(3,5-dinitrobenzoyl)-α-phenylglycinate

Silva

Nogueira

Santos

et al. 2015

Solar Energy Materials and Solar Cells

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Synthesis and electrochromic properties of oligothiophene derivatives

Cited by 32 publications

References 7 publications

Synthesis and photovoltaic properties of alkoxy-benzimidazole containing low band gap polymers

Synthesis and photovoltaic properties of alkoxy-benzimidazole containing low band gap polymers

Synthesis and Characterization of Tetraaniline-Polyethylene Glycol Block and Star-shaped Copolymers

Copolymerisation as a way to enhance the electrochromic properties of an alkylthiophene oligomer and a pyrrole derivative: copolymer of 3,3′″ dihexyl-2,2′:5′,2″:5″,2′″-quaterthiophene with (R)-(-)-3-(1-pyrrolyl)propyl-N-(3,5-dinitrobenzoyl)-α-phenylglycinate

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