125143-53-5Relevant articles and documents
Synthesis, characterization, and transistor response of semiconducting silole polymers with substantial hole mobility and air stability. Experiment and theory
Lu, Gang,Usta, Hakan,Risko, Chad,Wang, Lian,Facchetti, Antonio,Ratner, Mark A.,Marks, Tobin J.
, p. 7670 - 7685 (2008)
Realizing p-channel semiconducting polymers with good hole mobility, solution processibility, and air stability is an important step forward in the chemical manipulation of charge transport in polymeric solids and in the development of low-cost printed electronics. We report here the synthesis and full characterization of the dithienosilole- and dibenzosilole-based homopolymers, poly(4,4-di-n-hexyldithienosilole) (TS6) and poly(9,9-di-n- octyldibenzosilole) (BS8), and their mono- and bithiophene copolymers, poly(4,4-di-n-hexyldithienosilole-alt-(bi)thiophene) (TS6T1, TS6T2) and poly(9,9-di-n-octyldibenzosilole-alt-(bi)thiophene) (BS8T1,BS8T2), and examine in detail the consequences of introducing dithienosilole and dibenzosilole cores into a thiophene polymer backbone. We demonstrate air-stable thin-film transistors (TFTs) fabricated under ambient conditions having hole mobilities as large as 0.08 cm2/V·s, low turn-on voltages, and current on/off ratios > 106. Additionally, unencapsulated TFTs fabricated under ambient conditions are air-stable, an important advance over regioregular poly(3-hexylthiophene) (P3HT)-based devices. Density functional theory calculations provide detailed insight into the polymer physicochemical and charge transport characteristics. A direct correlation between the hole injection barrier and both TFT turn-on voltage and TFT polymer hole mobility is identified and discussed, in combination with thin-film morphological characteristics, to explain the observed OTFT performance trends.
Very large silacylic substituent effects on response in silole-based polymer transistors
Huang, Hui,Youn, Jangdae,Ponce Ortiz, Rocio,Zheng, Yan,Facchetti, Antonio,Marks, Tobin
, p. 2185 - 2200 (2011)
Understanding the interrelationships between molecular structure and organic thin film transistor performance is key to the realization of novel organic semiconductors achieving superior device characteristics. Herein we report the synthesis, characterization, and charge-transporting properties in organic field-effect transistors (OFETs) of dithieno silole-based oligomers and copolymers having silacycloalkyl substituents. Silacyclization of the alkyl substituents on the silole silicon atom reduces steric encumbrance, contracts solid state intermolecular π-π contacts, and enhances the charge-transport capacity of the oligomers. Oligomer 3,3′-dihexylsilylene-2,2′:5, 2′′:5′,2′′′:5′′, 2′′′′:5′′′,2′′′ ′′-sexithiophene (SM5) with two Si-n-hexyl substituents is not FET-active, while the mobilities of 3,3′-cyclopentanylsilylene-2,2′: 5,2′′:5′,2′′′:5′′, 2′′′′:5′′′,2′′′ ′′′-sexithiophene (SM4) and 3,3′-cyclobutysilylene-2, 2′:5,2′′:5′,2′′′:5′′, 2′′′′:5′′′,2′′′ ′′-sexithiophene (SM3) FETs are 2.6 × 10-4 and 3.4 × 10-4 cm2/(V s), respectively. Single crystal structural data and melting point derived intermolecular packing trends parallel these FET results. Copolymers P1-P4 based on the same dithienosilole cycloalkyl cores exhibit optimized hole mobilities of 2 × 10-5, 6 × 10-4, 3 × 10-4, and 2 × 10-3 cm2/V?s, respectively, lower than that of analogous silole-containing polymers with long Si-alkyl substituents, implying that the solubilizing and self-assembly functions of Si-alkyl substituents are important for optimizing the mobility. Interestingly, copolymer [poly{[N,N′-bis(2- octyl-dodecyl)-1,4,5,8-naphthalenedicarboximide-2,6-diyl]-alt-5,5′-(3, 3′-cyclopentanylsilylene-2,2′-bithiophene (P5) films are the most ordered and exhibit a good electron mobility of 4 × 10-3 cm2/V?s after thermal annealing. All of these OFETs exhibit good ambient-stability, which is attributed to their low-lying HOMOs (>0.2 eV lower than that of P3HT), a consequence of introducing silole cores into polythiophene backbones.
Synthesis and characterization of conjugated low band-gap terpolymers incorporating carbazole for photovoltaic application
Kim, Ki-Won,Na, Hyungjun,So, Won-Wook,Yoon, Sung Cheol,Shin, Won Suk
, p. 4279 - 4283 (2012)
A series of photoactive conjugated low band-gap copolymer (CPSB) and terpolyemrs (TPSBCz-n, n = 1 to 4) based on N-alkyl carbazole, 4,4'-dialkyl dithienosilole, and bezothiadiazole were synthesized. The copolymer and terpolymers were built with the fraction of the carbazole unit varied for 0, 2.5, 5, 10 and 25 mol%. Among the mixtures, the composition of 25 wt% of terpolymer bearing 10 mol.% of the carbazole unit, TPSBCz-3, and 75 wt% of C71-PCBM found a power conversion efficiency of 0.86% with a open-circuit voltage of 0.59 V, the short-circuit current of 4.85 mA and fill factor of 0.30 under AM 1.5 spectral illumination. Our findings suggest that terpolymer bearing low concentration of carbazole lead to a high power conversion efficiency with improved the short-circuit current due to hole mobility enhancement effect of carbazole unit. Copyright
Designing conducting polymer-based sensors: selective ionochromic response in Crown Ether containing polythiophenes
Marsella, Michael J.,Swager, Timothy M.
, p. 12214 - 12215 (1993)
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Preparation and properties of thienyl and 2,2'-substituted cobalt-bis(semiquinone) tautomers
O'Sullivan, Thomas J.,Djukic, Brandon,Dube, Paul A.,Lemaire, Martin T.
, p. 533 - 538 (2009)
The synthesis and characterization of two new 2,2'-bipyridine ligands containing 3-ethynylthiophene and 3,3'-diethynyl-2,2'-bithiophene substituents is presented, along with the preparation, electronic, and magnetic properties of monoand bimetallic cobalt-semiquinone valence tautomers containing these ligands.
Selective halogenation of bithiophenes using 2-halopyridazin-3(2H)-ones under ambient conditions
Jung, Kwang-Ju,Seung, Beom Kang,Won, Ju-Eun,Park, Song-Eun,Ki, Hun Park,Jong, Keun Park,Lee, Sang-Gyeong,Yoon, Yong-Jin
, p. 490 - 494 (2009)
2,2′-Bithiophene and halogenated-2,2′-bithiophenes were halogenated with 2-halo-4,5-dichloropyridazin-3(2H)-one in the presence of zinc halide to give selectively the corresponding dihalo-, trihalo-, and tetrahalo-2,2′-bithiophenes involving the same or different halogens in excellent yields, respectively. Georg Thieme Verlag Stuttgart.
Dithienosilole- and dibenzosilole-thiophene copolymers as semiconductors for organic thin-film transistors
Usta, Hakan,Lu, Gang,Facchetti, Antonio,Marks, Tobin J.
, p. 9034 - 9035 (2006)
The synthesis and physicochemical properties of a new class of thiophene/arenesilole-containing π-conjugated polymers are reported. Examples of this new polymer class include the following: poly(2,5-bis(3′,3′′-dihexylsilylene-2′,2′′-bithieno)thiophene) (TS6T1), poly(2,5′-bis(3′′,3′″-dihexylsilylene-2′′,2′″-bithieno)bithiophene) (TS6T2), poly(2,5′-bis(2′′,2′″-dioctylsilylene-1′′,1′″-biphenyl)thiophene) (BS8T1), and poly(2,5′-bis(2′′,2′″-dioctylsilylene-1′′,1′″-biphenyl)bithiophene) (BS8T2). Organic field-effect transistors (OFETs) with hole carrier mobilities as high as 0.02-0.06 cm2/V s in air, low turn-on voltages, and current on/off ratios >105-106 are fabricated using solution processing techniques with the above polymers as the active channel layer. OFETs based on this polymer class exhibit excellent ambient operational stability. Copyright
Dialkylthienosilole and N-alkyldithienopyrrole-based copolymers: Synthesis, characterization, and photophysical study
El-Shehawy, Ashraf A.,Abdo, Nabiha I.,El-Hendawy, Morad M.,Abdallah, Abdul-Rahman I.A.,Lee, Jae-Suk
, (2020/03/04)
We synthesized and characterized a set of D-π-A conjugated copolymers containing thiophene π-bridge. While benzothiadiazole serves as an acceptor (A) unit, the 4,4-dialkyldithieno[3,2-b:2′,3′-d]silole (DTSi) or N-alkyldithieno[3,2-b:2′,3′-d]pyrrole (DTP) act as a donor (D) unit. The copolymers were synthesized via the commonly Stille cross-coupling reaction and exhibited molecular weights of 18.6 to 31.3 kg/mol. The main structural differences among the copolymers are the type of donor moiety (DTSi or DTP) and the position of hexyl side chains on the thiophene π-bridge units between the D and A moieties. The ultimate goal of this work is to explore the effect of three structural factors that could control the photophysical properties of polymers in order to help in the rational design of polymers having specific properties used in optoelectronic devices. The physical properties include thermal stability, photophysical, and electrochemical properties. The structural factors are (a) the power of donor moiety, (b) the position of alkyl side chain on the thiophene π-bridge, and (c) the nature of the alkyl side chain. Also, we utilized the density functional theory calculations to calculate the geometric and electronic structures. A good agreement was remarked between the experimental and theoretical findings.
Cross-shaped small organic molecule hole transport material and preparation method
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Paragraph 0020-0022; 0031-0032; 0039-0041; 0050-0051, (2019/07/04)
The invention provides a cross-shaped small organic molecule hole transport material and a preparation method. The preparation method comprises the following steps: uniformly mixing 5-hexyl-5'-trimethyl-2,2'-bithiophene or 5-octyl-5'-trimethyl-2,2'-bithiophene with 3,3',5,5'-tetrabromo-2,2'-bithiophene in methylbenzene at a molar ratio of 1:(4-6); performing a reaction at the temperature of 90-120DEG C for 18-25h, cooling to room temperature and adding silica gel powder for spin drying; separating and purifying a coarse product after spin drying with dichloromethane and n-hexane at a ratio of1:(5-20) as an eluting agent to obtain the cross-shaped small organic molecule hole transport material which is shown in the structural formula I as shown in the specification or the structural formula II as shown in the specification. Due to the 'x' rotary cross-shaped structure of the hole transport material, the excessive crystallization can be effectively inhibited, so that a thiophene derivative have good solubility and excellent hole transport performance under the condition that no excessive alkyl substituted units are introduced; the current density and the photoelectric conversion efficiency of a device can be greatly improved after the cross-shaped small organic molecule hole transport material is applied in an all-inorganic perovskite solar cell.
