- D-A-D structured selenadiazolesbenzothiadiazole-based near-infrared dye for enhanced photoacoustic imaging and photothermal cancer therapy
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Near-infrared (NIR) small molecular organic dyes as photothermal agents for cancer photothermal therapy (PTT) have attracted considerable research attention. Herein, two donor-acceptor-donor (D-A-D) structured NIR dyes, BBTT and SeBTT, are rationally designed, where the only difference is one heteroatom within the acceptor unit varying from sulfur to selenium (Se). More importantly, SeBTT NPs exhibit stronger NIR absorbance and higher photothermal conversion efficiency (PTCE ≈ 65.3%). In vivo experiments illustrate that SeBTT NPs can be utilized as a high contrast photoacoustic imaging (PAI) agent, and succeed in tumor suppression without noticeable damage to main organs under NIR photoirradiation. This study presents an effective molecular heteroatom surgery strategy to regulate the photothermal properties of NIR small molecules for enhanced PAI and PTT.
- Cheng, Zijin,Zhang, Tian,Wang, Weili,Shen, Qing,Hong, Ying,Shao, Jinjun,Xie, Xiaoji,Fei, Zhenghao,Dong, Xiaochen
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Read Online
- Fluorene ring group-containing non-condensed ring organic small molecular material and preparation method and application thereof
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The invention relates to a fluorene ring group-containing non-condensed ring organic small molecular material and a preparation method and an application thereof. 2, 7-di(4, 4, 5, 5-tetramethyl-1, 3-dioxo-2-borane)-9, 9-dioctyl fluorene is used as a central core unit, and a thiophene unit is introduced to enhance [pi] conjugation of a molecular main chain, on this basis, benzothiadiazole is introduced to increase the electron deficiency capacity of the obtained molecule, thiophene units are connected to the two sides to expand conjugation and finally reduce the energy band gap of the molecule, side chains on thiophene can improve the solubility of the molecule, and fluorine-containing cyanoindanone units are connected to the two ends to form effective charge transfer in the whole molecule.
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Paragraph 0083-0089
(2021/04/07)
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- Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges
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Four novel benzo[c][1,2,5]thiadiazole comprising monomers namely 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TBTT), 5-fluoro-4,7-bis(4-hexylthiophen-2-yl)-6-((2-octyldodecyl)oxy)benzo[c][1,2,5]thiadiazole (HTBTHT), 5-fluoro-4,7-di(furan-2-yl)-6-((2-octyldodecyl)oxy)benzo- [c][1,2,5]thiadiazole (FBTF), and 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-bis(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TTBTTT) were designed, and synthesized successfully via Stille polycondensation reaction. The structural characterizations of the monomers were performed by 1H and 13C NMR spectroscopy and High Resolution Mass Spectroscopy (HRMS). The monomers were then electropolymerized in a three electrode cell system via cyclic voltammetry. The electrochemical, and spectroelectrochemical characterization of the polymers were reported in detail. Besides, theoretical calculations were performed to elucidate observed experimental properties. According to the cyclic voltammogram of the polymers, HOMO and LUMO energy levels were calculated as -5.68 eV/-3.91 eV, -5.71 eV/-3.72 eV, -5.61 eV/-4.04 eV, and -5.51 eV/-3.71 eV and the electronic band gaps were 1.77 eV, 1.99 eV, 1.57 eV, and 1.80 eV for PTBTT, PHTBTHT, PFBTF, and PTTBTTT, respectively.
- Karaman, Cansu Zeytun,G?ker, Seza,Hacio?lu, Serife O.,Haciefendio?lu, Tu?ba,Yildirim, Erol,Toppare, Levent
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- Synthesis of selenophene substituted benzodithiophene and fluorinated benzothiadiazole based conjugated polymers for organic solar cell applications
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A series of alternating conjugated copolymers which contain selenophene modified benzodithiophene and fluorine bearing benzothiadiazole have been synthesized via Stille polycondensation reaction to investigate the effect of the number of fluorine atoms substituted to the benzothiadiazole. Three different polymers, PBDTSe-BT, PBDTSe-FBT and PBDTSe-FFBT, were reported and their electrochemical, spectroelectrochemical, and photovoltaic behaviors were examined. Density functional theory calculations were performed on model tetramer structures to shed light on how substituting the fluorine atom to the acceptor building block affects the structural, electronic and optical properties of the polymers. The results of computational studies were compared with experimental studies. The structure adjustment accomplished by fluorine substitution on the benzothiadiazole moiety reveals an influence on the electronic structure of polymers with a more negative HOMO energy level. A high VOC for the resulting photovoltaic device was examined for PBDTSe-FFBT. Difluorinated polymer PBDTSe-FFBT:PC71BM organic solar cell exhibited the highest photovoltaic performance of 2.63% with JSC of 7.24 mA cm-2, VOC of 0.72 V and FF of 50.6%. PBDTSe-BT:PC71BM revealed the best PCE as 2.39%, and the device reached the highest efficiency up to 1.68% for PBDTSe-FBT:PC71BM.
- Aslan, Sultan Taskaya,Cevher, Duygu,Bolay?r, Eda,Hizalan Ozsoy, Gonul,Arslan Udum, Yasemin,Y?ld?r?m, Erol,Toppare, Levent,Cirpan, Ali
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- Planar and twisted molecular structure leads to the high brightness of semiconducting polymer nanoparticles for NIR-IIa fluorescence imaging
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Semiconducting polymer nanoparticles (SPNs) emitting in the second near-infrared window (NIR-II, 1000-1700 nm) are promising materials for deep-tissue optical imaging in mammals, but the brightness is far from satisfactory. Herein, we developed a molecular design strategy to boost the brightness of NIR-II SPNs: structure planarization and twisting. By integration of the strong absorption coefficient inherited from planar π-conjugated units and high solid-state quantum yield (φPL) from twisted motifs into one polymer, a rise in brightness was obtained. The resulting pNIR-4 with both twisted and planar structure displayed improved φPL and absorption when compared to the planar polymer pNIR-1 and the twisted polymer pNIR-2. Given the emission tail extending into the NIR-IIa region (1300-1400 nm) of the pNIR-4 nanoparticles, NIR-IIa fluorescence imaging of blood vessels with enhanced clarity was observed. Moreover, a pH-responsive poly(β-amino ester) made pNIR-4 specifically accumulate at tumor sites, allowing NIR-IIa fluorescence image-guided cancer precision resection. This study provides a molecular design strategy for developing highly bright fluorophores.
- Liu, Shunjie,Ou, Hanlin,Li, Yuanyuan,Zhang, Haoke,Liu, Junkai,Lu, Xuefeng,Kwok, Ryan T.K.,Lam, Jacky W.Y.,Ding, Dan,Tang, Ben Zhong
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supporting information
p. 15146 - 15156
(2020/10/13)
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- Highly fluorescent triazolopyridine-thiophene D-A-D oligomers for efficient pH sensing both in solution and in the solid state
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Conjugated fluorophores have been extensively used for fluorescence sensing of various substances in the field of life processes and environmental science, due to their noninvasiveness, sensitivity, simplicity and rapidity. Most existing conjugated fluorophores exhibit excellent light-emitting performance in dilute solutions, but their properties substantially decrease or even completely vanish due to severe aggregation quenching in the solid state. Herein, we synthesize a series of triazolopyridine-thiophene donor-acceptor-donor (D-A-D) type conjugated molecules with high absolute fluorescence quantum yields (ΦF) ranging from 80% to 89% in solution. These molecules also show unusual light-emitting properties in the solid state with ΦF of up to 26%. We find that owing to the protonation-deprotonation process of the pyridine ring, these compounds display obvious changes in both fluorescence wavelength and intensity upon addition of acids, and these changes can be readily recovered by the successive introduction of bases. By harnessing this phenomenon, we further show that these fluorophores can be employed for efficient and reversible fluorescence sensing of hydrogen ions in a broad pH range (0.0-7.0). With the fabrication of pH testing papers and ink-printed complex patterns including butterflies and letters on substrates, we demonstrate the application of such sensors to fluorescence indication or solid state pH detection for real samples such as volatile acidic/basic gas and water-quality analysis.
- Jian, Nannan,Qu, Kai,Gu, Hua,Zou, Lie,Liu, Ximei,Hu, Faqi,Xu, Jingkun,Yu, Yan,Lu, Baoyang
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p. 7174 - 7182
(2019/04/04)
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- Selenium-containing near-infrared organic semiconductor as well as preparation method and application thereof
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The invention relates to a selenium-containing near-infrared organic semiconductor as well as a preparation method and application of the organic semiconductor to photothermal therapy of tumor. The organic semiconductor is characterized in that selenium atoms are introduced into benzothiadiazole units; the selenium atoms have high polarizability; the spectrum moves to a long-wavelength direction;through the organic semiconductor, an organic nano material with absorption wavelength (an ultraviolet absorption wavelength reaches up to 906nm, and a fluorescence emission wavelength reaches up to 1040nm) in a near-infrared area is obtained by a re-precipitation method; the nano reagent has high photothermal conversion efficiency, excellent water dispersibility, excellent tumor tissue targetingproperty and high biological compatibility, can be applied to therapy of tumor cells and living organisms, and is capable of effectively inhibiting the growth of the tumor cells and effectively inhibiting metastasis of tumor cells so as to achieve the photothermal therapy effect of the tumor, so that the nano reagent has great application prospects in the field of tumor therapy.
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Paragraph 0043; 0045; 0052
(2018/07/06)
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- A fast response of nitric oxide near-infrared probe and its preparation and biological applications (by machine translation)
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The invention relates to a fast response of nitric oxide near-infrared probe and its preparation and biological application, the structure shown in formula (I), which belongs to the field of organic fluorescent probe. This invention is designed and has synthesized a kind of fast response of the near-infrared nitric oxide probe. The probe is after NO response with near-infrared emission. In vitro experimental study shows that, probe and NO fast reaction speed. In the physiological conditions (pH 7.4) next, probe stability, and to NO has higher sensitivity, selectivity and interference. Biological experimental study shows that, probe not only can be applied to the cell in the level of endogenous NO detection, can also be applied to PD cell and Drosophila brain model in NO level of detection. These results indicate that, the probe has a relatively high specificity, selectivity, stability, which may be applied to the early diagnosis of Parkinson's disease. (by machine translation)
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Paragraph 0044-0046
(2018/12/14)
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- Alkyl chain thienyl seaver alkali and its synthesis method (by machine translation)
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This invention relates to alkyl chain thienyl Sievert alkali and synthetic method, thienyl Sievert alkali of the alkyl chain of the formula Alkyl chain thienyl Sievert alkali preparation method: (1) by the alkyl chain thiophene synthetic intermediates I;
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Paragraph 0039; 0045-0047
(2019/01/08)
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- Syntheses and photovoltaic properties of 6-(2-thienyl)-4H-thieno[3,2-b]indole based conjugated polymers containing fluorinated benzothiadiazole
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In this report, a series of copolymers based on 6-(2-thienyl)-4H-thieno[3,2-b]indole (TTI) as an electron-rich unit and fluorinated DTBT as an electron-deficient unit were synthesized, namely PTTIF1 and PTTIF2, and applied to photovoltaic devices. TTI unit was coupled with fluorinated DTBT to utilize the merit of introduction of fluorine atom leading to the lowering of the HOMO energy level while keeping high planarity of the conjugated backbone. The synthesized copolymers show a noticeable change in HOMO energy levels as compared with non-fluorinated polymer (PTTIDTBT-h). Optimized photovoltaic devices of PTTIF2 exhibited power conversion efficiency of 4.36% with decent JSC and FF values, which can be explained by the higher charge transporting ability of PTTIF2 with preferable face-on crystallite population than PTTIF1 in grazing incident wide-angle X-ray scattering (GIWAXS).
- Jeong, Ina,Chae, Sangmin,Yi, Ahra,Kim, Juae,Chun, Ho Hwan,Cho, Jung Hyeong,Kim, Hyo Jung,Suh, Hongsuk
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p. 115 - 125
(2016/12/30)
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- A novel ternary memory property achieved through rational introduction of end-capping naphthalimide acceptors
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Small molecule-based multilevel rewritable memory devices have recently gained extensive attention because they possess super-high storage density and can sustain the stored data without power supply and erase and rewrite electrically; however, small molecule-based multilevel flash-type memory device is extremely challenging to achieve. Herein, we designed a symmetric molecule with end-capping naphthalimide acceptors through rational tuning. This molecule showed an improved crystal size and uniform crystal orientation in the film state. The sandwich-structured device exhibited the typical WORM (write-once-read-many times) memory property from OFF to ON1 transition and encouraging flash memory behavior for the ON1/ON2 transition. This is the first report on small molecule-based ternary memory devices with rewritable memory behavior, and this study will inspire the exploration of multilevel data-storage devices with fully rewritable properties in the subsequent researches.
- Zhang, Qijian,He, Jinghui,Li, Hua,Li, Najun,Xu, Qingfeng,Chen, Dongyun,Lu, Jianmei
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supporting information
p. 7961 - 7968
(2017/08/17)
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- A star-shaped small molecule and its synthetic method and application
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The invention discloses a triphenylamine-based star-shaped small molecule as well as a synthesis method and application thereof. The preparation process comprises the following steps: adding n-butyltin chloride SnClBu3 into 3-hexylthiophene to obtain a ti
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Paragraph 0034-0036
(2017/08/25)
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- Double-S, S - dioxo - dibenzo thiophene and five-membered ring monomer and its preparation method and polymer
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The invention discloses a bis S,S-dioxo-dibenzothiophene five-membered ring monomer, a preparation method thereof and a polymer. Due to a bis sulfonyl group in the bis S,S-dioxo-dibenzothiophene five-membered ring, the electron affinity of molecules can be improved more easily. By introducing an alkyl chain to the five-membered ring, the solubility of the monomer in organic solvent can be significantly improved, and meanwhile the steric hindrance influence on polymerization reaction from the position of the alkyl chain can be avoided. Due to a large conjugate plane, the cavitation and electron transmission performance of the polymer can be improved. Through Suzuki or Stille or Yamamotor polymerization reaction of the bis S,S-dioxo-dibenzothiophene five-membered ring monomer, a homopolymer or copolymer can be obtained. The polymer of the series has good solubility in organic solvent and is suitable for solution processing. The bis S,S-dioxo-dibenzothiophene five-membered ring monomer has broad application prospects in the fields of organic light-emitting display, organic photovoltaic cells and organic field effect transistors.
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Paragraph 0128
(2018/01/11)
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- 'Donor-free' oligo(3-hexylthiophene) dyes for efficient dye-sensitized solar cells
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The common trend in designing dyes for use in DSSCs with iodide-based electrolyte is based on a donor-π spacer-acceptor (D-π-A) architecture. Here, we report two 'donor-free' cyanoacrylic end-functionalized oligo(3-hexylthiophene) dyes (5T and 6T). Despite having no donor group, both dyes show reversible first oxidation process. Both 5T and 6T have n-hexyl alkyl chains to retard aggregation at different positions as well as different numbers of thiophene moieties. However, the dyes showed similar absorption properties and redox potentials. The DSSCs based on these dyes give power conversion efficiencies of more than 7%, although a significant difference in the VOC and FF has been observed. Using electrochemical impedance spectroscopy, this is attributed to the presence of more trap states when 6T attaches to TiO2 and modifies the surface, mainly affecting the fill factor. Overall, these dyes introduce a new and effective design concept for liquid-electrolyte DSSC sensitisers.
- Hu, Yue,Ivaturi, Aruna,Planells, Miquel,Boldrini, Chiara L.,Biroli, Alessio Orbelli,Robertson, Neil
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supporting information
p. 2509 - 2516
(2016/02/20)
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- Comparison of two strategies to improve organic ternary memory performance: 3-Hexylthiophene linkage and fluorine substitution
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In this paper, two acceptor-donor-acceptor (A-D-A) type organic small molecules, 4,4'-(5,5'-(benzo[c] [1,2,5]thiadiazole-4,7-diyl)bis(3-hexylthiophene-5,2-diyl))bis(N-(4-nitrophenyl)-N-phenylaniline) (NTPA2TBT) and 4,4'-(5,6-difluorobenzo[c] [1,2,5]thiadiazole-4,7-diyl)bis(N-(4-nitrophenyl)-N-phenylaniline) (NTPA2BTF2), were synthesized and fabricated into resistive random access memory devices. Compared with our previously reported molecule NTPA2BT, NTPA2TBT has 3-hexylthiophene linkages bridging its donor and acceptor, while there are two additional fluorine atoms in the benzothiadiazole moiety for NTPA2BTF2. Both the fabricated memory devices based on these two new molecules perform nonvolatile ternary memory characteristics with lower threshold voltages, higher reproducibility and better stability. The addition of 3-hexylthiophene bridges significantly promotes the planarity of the conjugation backbone and facilitates the molecular stacking, while the substitution hydrogen by fluorine improves the intermolecular interaction, and thus also induces an ordered molecular stacking. The insertion of 3-hexylthiophene bridges or fluorine atoms could be an effective strategy of tailoring organic molecules to improve data storage performance with lower power consumption.
- Bao, Qing,Li, Hua,Li, Yang,He, Jinghui,Xu, Qingfeng,Li, Najun,Chen, Dongyun,Wang, Lihua,Lu, Jianmei
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p. 306 - 313
(2016/04/19)
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- Can aliphatic anchoring groups be utilised with dyes for p-type dye sensitized solar cells?
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A series of novel laterally anchoring tetrahydroquinoline derivatives have been synthesized and investigated for their use in NiO-based p-type dye-sensitized solar cells. The kinetics of charge injection and recombination at the NiO-dye interface for these dyes have been thoroughly investigated using picosecond transient absorption and time-resolved infrared measurements. It was revealed that despite the anchoring unit being electronically decoupled from the dye structure, charge injection occurred on a sub picosecond timescale. However, rapid recombination was also observed due to the close proximity of the electron acceptor on the dyes to the NiO surface, ultimately limiting the performance of the p-DSCs.
- Hao, Yan,Wood, Christopher J.,Clark, Charlotte A.,Calladine, James A.,Horvath, Raphael,Hanson-Heine, Magnus W. D.,Sun, Xue-Zhong,Clark, Ian P.,Towrie, Michael,George, Michael W.,Yang, Xichuan,Sun, Licheng,Gibson, Elizabeth A.
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p. 7708 - 7719
(2016/05/24)
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- Benzocarbazoles three thiophene compound and its preparation and use
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The invention relates to benzo terthiophene compound as well as a preparation method and usage thereof. The structure of the benzo terthiophene compound is expressed by a formula I, and in the formula, the definition of X is described in the description.
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Paragraph 0133-0135
(2016/11/07)
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- Quinoxaline-based polymer dots with ultrabright red to near-infrared fluorescence for in vivo biological imaging
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This article describes the design and synthesis of quinoxaline-based semiconducting polymer dots (Pdots) that exhibit near-infrared fluorescence, ultrahigh brightness, large Stokes shifts, and excellent cellular targeting capability. We also introduced fluorine atoms and long alkyl chains into polymer backbones and systematically investigated their effect on the fluorescence quantum yields of Pdots. These new series of quinoxaline-based Pdots have a fluorescence quantum yield as high as 47% with a Stokes shift larger than 150 nm. Single-particle analysis reveals that the average per-particle brightness of the Pdots is at least 6 times higher than that of the commercially available quantum dots. We further demonstrated the use of this new class of quinoxaline-based Pdots for effective and specific cellular and subcellular labeling without any noticeable nonspecific binding. Moreover, the cytotoxicity of Pdots were evaluated on HeLa cells and zebrafish embryos to demonstrate their great biocompatibility. By taking advantage of their extreme brightness and minimal cytotoxicity, we performed, for the first time, in vivo microangiography imaging on living zebrafish embryos using Pdots. These quinoxaline-based NIR-fluorescent Pdots are anticipated to find broad use in a variety of in vitro and in vivo biological research.
- Liu, Hong-Yi,Wu, Pei-Jing,Kuo, Shih-Yu,Chen, Chuan-Pin,Chang, En-Hao,Wu, Chang-Yi,Chan, Yang-Hsiang
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p. 10420 - 10429
(2015/09/01)
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- Synthesis of EDOT -containing polythiophenes and their properties in relation to the composition ratio of EDOT
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Polythiophenes composed of 3,4-ethylenedioxythiophene (EDOT) and 3-hexylthiophene with different composition ratios of EDOT in the repeat unit of the polymer backbone are synthesized by polycondensation reactions. The optical and electrochemical properties of the polymers are compared with those of poly(3,4-ethylenedioxythiophene) and poly(3-hexylthiophene), and they are found to be well correlated with the EDOT composition ratio. In addition, the charge transport properties of the polymer films, measured using the in situ conductivity technique, are discussed in terms of the EDOT composition ratio, regioregularity, and the doping level.
- Imae, Ichiro,Ogino, Ryo,Tsuboi, Yoshiaki,Goto, Tatsunari,Komaguchi, Kenji,Harima, Yutaka
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p. 84694 - 84702
(2015/10/28)
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- Synthesis and photovoltaic properties of solution-processable star-shaped small molecules with triphenylamine as the core and alkyl cyanoacetate or 3-ethylrhodanine as the end-group
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Two novel star-shaped donor-acceptor small molecules, TPA-TBT-CN and TPA-TBT-R, with triphenylamine (TPA) as the core, benzothiadiazole (BT) as the arm, and alkyl cyanoacetate or 3-ethylrhodanine as the end-group are synthesized for application as donor m
- Hu, Zhao,Li, Xiao-Dong,Zhang, Wenjun,Liang, Aihui,Ye, Dandan,Liu, Zhitian,Liu, Jing,Liu, Yanjiao,Fang, Junfeng
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p. 5591 - 5597
(2014/01/23)
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- Benzoselenadiazole fluorescent probes-near-ir optical and ratiometric fluorescence sensor for fluoride ion
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A highly selective and sensitive near-IR optical sensor, benzoselenadiazole based diarylamine (TBS-HN), for fluoride (F-) has been designed and synthesized. TBS-HN also shows turn-on ratiometric fluorescence signaling in the presence of F-by inhibiting th
- Saravanan, Chinnusamy,Easwaramoorthi, Shanmugam,Hsiow, Chuen-Yo,Wang, Karen,Hayashi, Michitoshi,Wang, Leeyih
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supporting information
p. 354 - 357
(2014/04/03)
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- Effect of side-chain architecture on the optical and crystalline properties of two-dimensional polythiophenes
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The present study reported here synthesis of three novel two-dimensional (2D) polythiophene derivatives with conjugated terthiophene-vinylene side chain - poly{3-(5″-hexyl-2,2′:5′,2″-terthiophenyl-5-vinyl) thiophene-alt-thiophene} (P1), poly{3-(5,5″-dihexyl-2,2′:5′, 2″-terthiophenyl-3′-vinyl)thiophene-alt-thiophene} (P2), and poly{3-(4,4″-dihexyl-2,2:5′,2″-terthiophene-3′-vinyl) thiophene-alt-thiophene} (P3) - that were synthesized via stille coupling reaction. The terthiophene side chain with different conformations conjugated to the polythiophene main chain via vinyl linkage provided the ability to control the molecular organization, hence affecting the optoelectronic and electrochemical properties of 2D polymers. TD-DFT calculation with the B3LYP/6-31+g(d) function on electronic structures of the monomers was consistent with the experimental results. It suggested that the energetic states of HOMO and LUMO were highly dependent on the side-chain architectures. These polythiophene thin films fabricated by spin-casting show a broader absorption ranges from 300 to 700 nm which was significantly wider than the absorption of pure poly(3-hexylthiophene). When comparing the solid-state absorption spectra of these polymers before and after thermal annealing, P3 displayed the most red-shift in the wavelength range between 450 and 700 nm. It was presumably due to an extended conjugation length resulting from the linear conformation and preferred chain packing, as manifested in the X-ray diffraction. Molecular dynamics (MD) simulation on polymers with different side chains in isolated and packed states suggests planar conformation of the main chain was adopted and regulated by the side chains which were placed in parallel with the main-chain direction. Interestingly, P1 solution revealed an excitation-dependent emission property, suggesting a structural inhomogeneity in solution. Contrary to P1, the PL spectra of P2 and P3 showed only one emission peak at 460 nm, regardless of the excitation energy. Orientation and regiochemistry of the terthiophene side chain had a major impact on the overall optical and electronic properties of the polymer. Moreover, the HOMO and LUMO of these three polymers had been determined through cyclic voltammetry. HOMO of the three polymers were in the following order: P1 > P2 > P3. It implied that the energy level was regiochemistry dependent and directly associated with the linked position between backbone and conjugated side chain. Most importantly, through mesogen-jacketed-like design strategy employed in the present study, the improved packing of these two-dimensional polymers offered insights into structure design to enhance properties that have strong ties to the electronic devices.
- Kuo, Cheng-Yu,Huang, Yu-Chen,Hsiow, Chuen-Yo,Yang, Yu-Wen,Huang, Ching-I,Rwei, Syang-Peng,Wang, Hsing-Lin,Wang, Leeyih
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p. 5985 - 5997
(2013/09/02)
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- "fibonacci's route" to regioregular oligo(3-hexylthiophene)s
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We describe a new synthetic approach to regioregular monodisperse oligo(3-alkylthiophene)s allowing for simple separation of regioregular material in gram quantities. The number of repeat units follows the Fibonacci numbers up to a length of 21. In a small adaption of this approach, introduction of a protecting group was used to synthesize an oligo(3-hexylthiophene) with 36 repeating units, the longest regioregular 3-hexylthiophene oligomer synthesized to date.
- Koch, Felix P. V.,Smith, Paul,Heeney, Martin
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supporting information
p. 13695 - 13698
(2013/10/01)
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- Concise synthesis of well-defined linear and branched oligothiophenes with nickel-catalyzed regiocontrolled cross-coupling of 3-substituted thiophenes by catalytically generated magnesium amide
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The synthesis of linear and branched oligothiophenes of well-defined structures is performed with regioselective deprotonation of 3-substituted thiophenes and nickel-catalyzed cross-coupling of the thus formed metalated species with a bromothiophene. The reaction of 3-hexylthiophene with EtMgCl and 2,2,6,6-tetramethylpiperidine (TMP-H, 10 mol %) induces the metalation selectively at the 5-position by use of the catalytically generated hindered magnesium amide (TMPMgCl) and the subsequent reaction of a 2-halo-3- hexylthiophene (bromide or chloride) in the presence of a nickel catalyst affords a head-to-tail (HT)-type dimer. By repeating the same sequence, the linear oligothiophene up to a 4-mer is synthesized in good yield. The reaction of 3-hexylthiophene with 2,3-dibromothiophene also takes place to afford a branched oligothiophene 3-mer in quantitative yield. The obtained 3-mer is also metalated at the sterically less-hindered position in a regioselective manner furnishing a 7-mer in >99 % yield after a further coupling reaction with 2,3-dibromothiophene. These dendrimers react with several multifunctionalized organic electrophiles, leading to a variety of branched oligothiophenes. Copyright
- Tanaka, Shota,Tanaka, Daiki,Tatsuta, Go,Murakami, Kohei,Tamba, Shunsuke,Sugie, Atsushi,Mori, Atsunori
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supporting information
p. 1658 - 1665
(2013/02/25)
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- Synthesis and electrochemical properties of a new benzimidazole derivative as the acceptor unit in donor-acceptor-donor type polymers
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A new benzimidazole unit, 4′-(tert-butyl)spiro[benzo[d]imidazole-2, 1′-cyclohexane] was synthesized and coupled with different donor units like 3-hexylthiophene and 3,4-ethylenedioxythiophene (EDOT) via Stille coupling. The donor-acceptor-donor (D-A-D) ty
- Ozelcaglayan, Ali Can,Sendur, Merve,Akbasoglu, Naime,Apaydin, Dogukan Hazar,Cirpan, Ali,Toppare, Levent
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scheme or table
p. 224 - 229
(2012/07/03)
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- Effect of conjugated core building block dibenzo[a,c]phenazine unit on π-conjugated electrochromic polymers: Red-shifted absorption
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A comparative investigation was undertaken for the electrosynthesis and electrochemical properties of three different electroactive polymers having a conjugated core building block, dibenzo[a,c]phenazine. A series of monomers has been synthesized as regards to thiophene based units; thiophene, 3-hexyl thiophene, and 3,4-ethylenedioxythiophene. The effects of different donor substituents on the polymers' electrochemical properties were examined by cyclic voltammetry. Introducing highly electron-donating (ethylene dioxy) group to the monomer enables solubility while also lowering the oxidation potential. The planarity of the monomer unit enhances π-stacking and consequently lowering the Eg from 2.4 eV (PHTP) to 1.7 (PTBP). Cyclic voltammetry and spectroelectrochemical measurements revealed that 2,7-bis(4-hexylthiophen-2-yl) dibenzo[a,c]phenazine (HTP) and 2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5- yl)dibenzo[a,c]phenazine (TBP) possessed electrochromic behavior. The colorimetry analysis revealed that while PTBP have a color change from red to blue, PHTP has yellow color at neutral state and blue color at oxidized state. Hence the presence of the phenazine derivative as the acceptor unit causes a red shift in the polymers' absorption to have a blue color.
- Unver, Elif Kose,Tarkuc, Simge,Udum, Yasemin Arslan,Tanyeli, Cihangir,Toppare, Levent
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experimental part
p. 1714 - 1720
(2011/03/22)
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