- New iridium(III) cyclometalates with extended absorption features for bulk heterojunction solar cells
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Two new iridium(III) cyclometalates (A and B) based on 2-[5-(9,9′-diethyl-9H-fluoren-7-yl)thienyl]-pyridine were synthesized, characterized and applied in bulk-heterojunction solar cells (BHJSCs). Their absorption, electrochemical, thermal and photovoltaic properties have been investigated. The results reveal that the replacement of phenyl ring by thienyl one can extend the absorption wavelength up to 530 nm, thus narrowing the energy gap (Eg) to 2.93 eV and 2.81 eV for A and B, respectively. These complexes exhibit excellent thermal stability with the onset decomposition temperature at 5% weight-loss (Td) of over 370 °C. The BHJSC device with A as donor blended with [6,6]-phenyl C61-butyric acid methyl ester (PCBM) gave the best power conversion efficiency (η) of 0.51%, with a short-circuit photocurrent density (Jsc) of 2.68 mA cm-2, an open-circuit photovoltage (Voc) of 0.66 V and a fill factor (ff) of 0.28 under illumination of an AM 1.5 solar cell simulator.
- Tan, Guiping,Liu, Peng,Wu, Hao,Yiu, Sze-Chun,Dai, Fengrong,Feng, Ying-Hsuan,Liu, Xiaotian,Qiu, Yongfu,Lo, Yih Hsing,Ho, Cheuk-Lam,Wong, Wai-Yeung
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Read Online
- A versatile color tuning strategy for iridium(III) and platinum(II) electrophosphors by shifting the charge-transfer states with an electron-deficient core
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By fusing an electron-deficient ring system with the phenyl ring of a 2-phenylpyridine (ppy)-type ligand, a new and synthetically versatile strategy for the phosphorescence color tuning of cyclometalated iridium(III) and platinum(II) metallophosphors has been established. Two robust red electrophosphors with enhanced electron-injection/electron-transporting features were prepared by using an electron-trapping fluoren-9-one chromophore in the ligand design. The thermal, photophysical, redox and electrophosphorescent properties of these complexes are reported. These exciting results can be attributed to a switch of the metal-to-ligand charge-transfer (MLCT) character of the transition from the pyridyl groups in the traditional IrIII or PtII ppy-type complexes to the electron-deficient ring core, and the spectral assignments corroborate well with the electrochemical data as well as the time-dependent density functional theory (TD-DFT) calculations. The electron-withdrawing character of the fused ring results in much more stable MLCT states, inducing a substantial red-shift of the triplet emission energy from yellow to red for the IrIII complex and even green to red for the PtII counterpart. Electrophosphorescent organic light-emitting devices (OLEDs) doped with these red emitters fabricated by using vacuum evaporation technique have been realized with reasonable performance. The Royal Society of Chemistry 2009.
- Zhou, Gui-Jiang,Wang, Qi,Wong, Wai-Yeung,Ma, Dongge,Wang, Lixiang,Lin, Zhenyang
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Read Online
- Cysteine and homocysteine chemosensor based on photochromic diarylethene with fluorine
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A new photochromic diarylethene with formyl and fluorene groups, 1-[2-methyl-5-(9,9-diethyl-fluoren-2-yl)-3-thienyl]-2-[(2-methyl-5-formyl)-3-thienyl]perfluorocyclopentene, has been synthesized and characterized with single-crystal X-ray diffraction. Due to the interaction between the formyl group in its ring-closed isomer with cysteine/homocysteine, there was an evident color change in its absorption spectrum from blue to pale yellow and light brick-red upon addition of cysteine and homocysteine, respectively. Moreover, it was revealed that no obvious interference was observed during the titrations with the mixtures of cysteine/homocysteine and other amino acids. These results indicated that the diarylethene could be used as a colorimetric sensor to recognize cysteine/homocysteine with high selectivity.
- Wang, Jingcheng,Ma, Lele,Liu, Gang,Ding, Haichang,Pu, Shouzhi
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Read Online
- Novel hole transport material applied to solid-state dye-sensitized solar cell
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According to the design of the invention, a trifluorene ammonia compound is applied as a hole transport material to a solid-state dye-sensitized solar cell. Compared with common Spiro-OMeTAD, the compound has the characteristics that the molecular structure is simple, the solubility in an organic solvent is good, the compound and cations do not generate spectral competition with a photosensitizerand the like. The compound has a proper HOMO energy level and can be used as a hole transport material to be applied to a solid-state dye-sensitized solar cell.
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Paragraph 0028-0030
(2020/08/18)
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- Asymmetric tris-heteroleptic iridium(iii) complexes containing three different 2-phenylpyridine-type ligands: A new strategy for improving the electroluminescence ability of phosphorescent emitters
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A series of asymmetric tris-heteroleptic Ir(iii) phosphorescent complexes adopting both IrLL′L′′ (Ir3-1 and Ir3-2) and IrLL′(acac) (Ir2-1 and Ir2-2) chemical constitution have been successfully prepared, where L, L′ and L′′ represent different ppy-type (2-phenylpyridine) ligands. The IrLL′L′′ asymmetric tris-heteroleptic Ir(iii) phosphorescent complexes Ir3-1 and Ir3-2 bearing three different ppy-type ligands can show better thermal stability, higher ΦP and improved ability of trapping both holes and electrons than IrLL′(acac) asymmetric analogs Ir2-1 and Ir2-2. Thanks to these advantages, Ir3-1 and Ir3-2, especially Ir3-2, can show phenomenal EL performance with a maximum external quantum efficiency (ηext) of 26.2%, a maximum current efficiency (ηL) of 88.7 cd A-1 and a maximum power efficiency (ηP) of 75.3 lm W-1, much higher than the data achieved by not only IrLL′(acac) asymmetric analogs Ir2-1 and Ir2-2, but also the traditional Ir(L)3 symmetric counterparts. To the best of our knowledge, these data represent the highest EL efficiencies ever achieved by the asymmetric ppy-type Ir(iii) phosphorescent complexes reported in the literature. All these encouraging results not only indicate the great potential of the unique asymmetric IrLL′L′′ structures bearing three different ppy-type ligands in improving the EL ability of ppy-type Ir(iii) phosphorescent emitters, but also represent important progress in the design and synthesis of new asymmetric ppy-type Ir(iii) phosphorescent complexes with high EL ability.
- Dang, Wanping,Yang, Xiaolong,Feng, Zhao,Sun, Yuanhui,Zhong, Daokun,Zhou, Guijiang,Wu, Zhaoxin,Wong, Wai-Yeung
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supporting information
p. 9453 - 9464
(2018/09/25)
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- Delayed fluorescence based phenanthroimidazoles as OLED emitters having electron transporting properties
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Three new phenanthroimidazole derivatives have been synthesised and their optical, electrochemical, and thermal properties evaluated with the purpose of using them for making of possible OLED materials. Synthesised compounds have fluorescence quantum yiel
- Nagaraju, Peethani,Madhu, Chakali,Mohanty, Maneesha Esther,Rao, Vaidya Jayathirtha
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p. 229 - 240
(2019/05/21)
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- Color-tunable thiazole-based iridium(III) complexes: Synthesis, characterization and their OLED applications
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With respect to the commonly used electron-deficient pyridyl group in the benchmark dopant Ir(ppy)3, incorporating the electron-rich thiazolyl group with different chromophores have not been extensively studied. In this paper, some iridium(III) complexes bearing functional ligands with the thiazolyl moiety were synthesized and characterized by1H and13C NMR, UV–Vis absorption and photoluminescence spectroscopy. The emission color of these thiazole-based Ir(III) complexes can be tuned from yellow to red and the best phosphorescent organic light-emitting device exhibited the maximum external quantum efficiency of 11.1%, current efficiency of 35.8 cd/A and power efficiency of 21.9 lm/W.
- Chau, Nga-Yuen,Ho, Po-Yu,Ho, Cheuk-Lam,Ma, Dongge,Wong, Wai-Yeung
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- Iridium-containing red metal complex, preparation method thereof, and organic electroluminescent device adopting complex
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The invention relates to an iridium-containing red metal complex, a preparation method thereof, and an organic electroluminescent device adopting the complex. The iridium-containing red metal complex has a structure represented by a formula shown in the specification, and R in the specification is an alkyl group, an aryl group, a substituted aryl group, a heterocyclic aryl group or a substituted heterocyclic aryl group. Compared with present phosphorescent materials, the iridium-containing red metal complex has the advantages of high light and heat stability, realization of long-term preservation, high photoluminescence and electroluminescence efficiency, simple synthesis technology and low cost, and is a red phosphorescent material with excellent performances.
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Paragraph 0145; 0146; 0147
(2016/10/10)
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- Imidazole derivatives [...] and its preparation method (by machine translation)
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This invention relates to a kind of a kind of [...] imidazole derivatives and method for preparing the same. The structure of this compound is the formula is: . This method is convenient, pervasive, economic. Type I in the organic photoelectric material and based on the analysis of the fluorescence detection has a broad application prospect in the field; in addition, because of such compounds are containing two nitrogen atom heterocyclic compound, has good biological activity, can also be used as a drug intermediate, preparing human, livestock anathematic drug. (by machine translation)
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Paragraph 0141; 0142; 0143
(2016/10/08)
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- Design, synthesis, and structural and spectroscopic studies of push-pull two-photon absorbing chromophores with acceptor groups of varying strength
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A new series of unsymmetrical diphenylaminofluorene-based chromophores with various strong π-electron acceptors were synthesized and fully characterized. The systematic alteration of the structural design facilitated the investigation of effects such as molecular symmetry and strength of electron-donating and/or -withdrawing termini have on optical nonlinearity. In order to determine the electronic and geometrical properties of the novel compounds, a thorough investigation was carried out by a combination of linear and nonlinear spectroscopic techniques, single-crystal X-ray diffraction, and quantum chemical calculations. Finally, on the basis of two-photon absorption (2PA) cross sections, the general trend for π-electron accepting ability, i.e., ability to accept charge transfer from diphenylamine was: 2-pyran-4-ylidene malononitrile (pyranone) > dicyanovinyl > bis(dicyanomethylidene)indane >1-(thiophen-2-yl)propenone > dicyanoethylenyl >3-(thiophen-2-yl)propenone. An analogue with the 2-pyran-4-ylidene malononitrile acceptor group exhibited a nearly 3-fold enhancement of the 2PA cross section (1650 GM at 840 nm), relative to other members of the series.
- Morales, Alma R.,Frazer, Andrew,Woodward, Adam W.,Ahn-White, Hyo-Yang,Fonari, Alexandr,Tongwa, Paul,Timofeeva, Tatiana,Belfield, Kevin D.
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p. 1014 - 1025
(2013/04/10)
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- Platinum-acetylide polymers with higher dimensionality for organic solar cells
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A new series of platinum(II)-acetylide polymers P1-P3 containing thiophene-triarylamine chromophores of different dimensions were synthesized and their electronic band structures, field-effect charge transport, and application in bulk heterojunction solar
- Wang, Qiwei,He, Zhicai,Wild, Andreas,Wu, Hongbin,Cao, Yong,Schubert, Ulrich S.,Chui, Chung-Hin,Wong, Wai-Yeung
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supporting information; experimental part
p. 1766 - 1777
(2011/12/16)
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- Red non-doped electroluminescent dyes based on arylamino fumaronitrile derivatives
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A diarylamine, 2-(phenylamino)-9,9-diethylfluorene and three red fluorescent dyes based on arylamino fumaronitrile derivatives, bis(4-(N-(1-naphthyl)phenylamino)-phenyl)fumaronitrile (1-NPAFN, 5a), bis(4-(N-(2-naphthyl)phenylamino)phenyl)-fumaronitrile (2-NPAFN, 5b) and bis(4-(N-(9,9-diethyl-2-fluorenyl)phenylamino)-phenyl)fumaronitrile (EFPAFN, 5c), were prepared. The red dyes showed strong red photoluminescence upon excitation which centered at around 635, 650, 658?nm for 1-NPAFN, 2-NPAFN and EFPAFN in solid film respectively. Fluorescence concentration quenching of red dyes was suppressed. Thermal stability and energy levels were also measured. Multilayer non-doped electroluminescent devices were fabricated using the red dyes (5b, 5c) as red emitters. Device performance kept relatively constant at a wide current density level in the range of 20-150?mA/cm2.
- Zhang, Wenguan,He, Zhiqun,Mu, Linping,Zou, Ye,Wang, Yongsheng,Zhao, Shengmin
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experimental part
p. 86 - 92
(2010/11/16)
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- Color pure and stable blue light emitting material containing anthracene and fluorene for OLED
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A new blue light emitting anthracene derivative, 9,10-bis-(9',9'-diethyl- 7'-t-butyl-fluoren-2'-yl)anthracene (BETF), has been designed and synthesized by a palladium catalyzed Suzuki cross-coupling. A theoretical calculation of the three-dimensional structure of BETF supports that it has a non coplanar structure and inhibited intermolecular interactions resulting in high luminescent efficiency and high color purity. BETF has good thermal stability with glass-transition temperature (Tg) of 131 °C. The PL maximum of BETF in solution and film were 438 nm and 440 nm, respectively, showing pure blue emission. A multilayer device using BETF as emitting material exhibits maximum luminescence efficiency of 2.2 cd/A and a pure blue emission (Commission Internationale de L'Eclairage (CIE) coordinates of x = 0.15, y = 0.10).
- Park, Hyuntae,Oh, Daehwan,Park, Jong-Won,Kim, Jin-Hak,Shin, Sung-Chul,Kim, Yun-Hi,Kwon, Soon-Ki
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scheme or table
p. 1951 - 1955
(2010/12/25)
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- Quantum amplified isomerization in polymers based on triplet chain reactions
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(Graph Presented) Photoinitiated triplet quantum amplified isomerizations (QAI) of substituted Dewar benzene derivatives in polymeric media are reported. The quantum efficiencies and the ultimate extents of reactant-to-product conversions increase significantly with the incorporation of appropriate co-sensitizers; compounds whose triplet energies are similar to or lower than that of the sensitizer and close to that of the reactant. These co-sensitizers serve to promote chain-propagating energy transfer processes and thereby increase the action sphere of photosensitization. Isomerization quantum yields increase, as predicted, with increasing concentrations of the reactants and the co-sensitizers. Chain amplifications as large as ~16 and extents of conversion that approach 100% have been achieved. Mechanistic schemes are proposed to account for the dynamics of the inherent energy transfer processes and provide a predictively useful model for the design of a new class of photoresponsive polymers based on changes in the refractive index of the materials.
- Ferrar, Lorraine,Mis, Mark,Dinnocenzo, Joseph P.,Farid, Samir,Merkel, Paul B.,Robello, Douglas R.
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p. 5683 - 5692
(2008/12/22)
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- Solution-processable organic fluorescent dyes for multicolor emission in organic light emitting diodes
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Four novel fluorescent dyes, bis(difluorenyl)amino-substituted carbazole 1, pyrene 2, perylene 3, and benzothiadiazole 4, were synthesized by C-N cross-coupling with a palladium catalyst. These dyes are soluble in common organic solvents, and their uniform films were formed by spin-coating from their solutions. Their glass transition temperatures were sufficiently high (120-181°C) to form amorphous films for organic light emitting diodes. These solution processable dyes exhibited strong photoluminescence (PL) in the film form (1: sky blue, 2: blue-green, 3: yellow, and 4: deep red). Optical and electrochemical properties of the compounds were investigated with photoelectron spectroscopy and cyclic voltammetry. The energy levels obtained from both measurements were in good agreement, and those levels were related to the electronic properties of the central core; the electron-donating carbazole compound showed the lowest ionization potential and the electron-withdrawing benzothiadiazole compound showed the largest electron affinity. Simple double layer devices were prepared with these fluorescent dyes as emitting layer and bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminium(iii) (BAlq) as a common hole blocking layer for each color. Electroluminescence colors were the same as those of the PL spectra in each compound. These multicolor electroluminescences show that these conjugated oligomers can be candidates for solution processable light emitting materials for OLEDs as well as conjugated polymers or dendrimers.
- Pu, Yong-Jin,Higashidate, Makoto,Nakayama, Ken-Ichi,Kido, Junji
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supporting information; experimental part
p. 4183 - 4188
(2010/03/03)
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- Synthesis and characterization of photoresponsive diphenylaminofluorene chromophore adducts of [60]fullerene
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A class of acceptor-keto-donor structures as hindered 9,9-di(3,5,5- trimethylhexyl)-2-diphenylaminofluoreno-methano[60]fullerene C 60(>DPAF-C9) and the related bisadducts C 60(>DPAF-C9)2 and C60
- Padmawar, Prashant A.,Canteenwala, Taizoon,Verma, Sarika,Tan, Loon-Seng,Chiang, Long Y.
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p. 1366 - 1378
(2007/10/03)
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- Synthesis of Alkylated Aminofluorenes by Palladium-Catalyzed Substitution at Halofluorenes
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New N-substituted 2-amino-9,9-dialkylfluorenes optionally bearing electron-withdrawing substituents such as nitro or cyano in position 7 can be synthesized starting from 2-halo-9,9-dialkylfluorenes by Pd-catalyzed substitution with amines. Chiral amino groups can be introduced by this method too. 2-N,N-Dimethylamino-7-nitro-9H-fluorene was obtained in a convenient way by reductive amination. The N-substituted 2-amino-7-nitro-9H-fluorenes are promising candidates for fluorescence probes for femtosecond solvation dynamics.
- Saroja, Ginagunta,Pingzhu, Zhang,Ernsting, Nikolaus P.,Liebscher, Juergen
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p. 987 - 990
(2007/10/03)
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- FULLERENE COMPOUNDS
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The invention relates to fullerene compounds of formula (I); in which X1, X2, X3, X4, X5, YI, Y2, V, W, F, E, R, r, n, p, and q are defined as in the specification. Also disclose
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- Synthesis of C60-diphenylaminofluorene dyad with large 2PA cross-sections and efficient intramolecular two-photon energy transfer
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The first, highly two-photon active C60 derivative comprised of a A-sp3-D conjugate structure was synthesized showing effective two-photon absorption cross-sections (σ2′ = 196×10-48 cm4 sec-1/su
- Chiang, Long Y.,Padmawar, Prashant A.,Canteenwala, Taizoon,Tan, Loon-Seng,He, Guang S.,Kannan, Ramamurthi,Vaia, Richard,Lin, Tzu-Chau,Zheng, Qingdong,Prasad, Paras N.
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p. 1854 - 1855
(2007/10/03)
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- Multi-armed chromophores with very large two-photon absorption cross-sections
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Provided are chromophores with very large two-photon absorption cross-sections. One group of these chromophores has the formula: (T—Q)n—N—Phm wherein Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-3 and m has a value of 3?n, and wherein T is wherein R1and R2are alkyl groups having 1 to 20 carbon atoms, provided that when Q is a single bond, the value of n is 2 or 3. Another group of these chromophores has the formula: (T—Q)n—G—Phm wherein T is as defined above, Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-4 and m has a value of 4?n, and wherein G is a 4-arm core unit. Yet another group of these chromophores has the formula: (T—Q)n—G—Phm wherein T is as described previously, Q is a single bond or 1,4-phenylene, Ph is a phenyl group, n has a value of 1-6 and m has a value of 6?n, and wherein G is a 6-arm core unit.
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- Benzothiazole-containing two-photon chromophores exhibiting strong frequency upconversion
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There are provided asymmetrical two-photon chromophores of the formula: D-Ar-A wherein Ar is selected from the group consisting of wherein Fl is a fluorene group of the formula: wherein R1 and R2 are alkyl groups having 2 to 20 carbon atoms, and wherein R1 and R2 are the same or different; wherein D is wherein Q is selected from the group consisting of -H, -OH and -O-CxH2x+1, wherein x has a value of 1 to 10; and wherein A is selected from the group consisting of wherein Z is selected from the group consisting of -O- and -S-.
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