Co-reporter:Jianghuai Hu;Rui Sun;Yihao Wu;Jiangbo Lv;Zhiping Wang;Ke Zeng
RSC Advances (2011-Present) 2017 vol. 7(Issue 69) pp:43978-43986
Publication Date(Web):2017/09/07
DOI:10.1039/C7RA06162E
Binary blends composed of benzimidazole-containing phthalonitrile (PNBI) and epoxy resin E51 were prepared. The PNBI/E51 (PE) blends showed good compatibilities and unique synergistic curing behaviors on full consumption of nitrile groups (PE19, PNBI:E51 = 1 : 9 in weight ratio) and epoxy groups in the view of DSC, rheology and IR. Curing procedures of the PE blends were determined by DSC and DMA. Studies on the curing procedure showed that the PE blends exhibited good processability and could be fully cured at a temperature lower than 210 °C. Studies on the cured PE blends showed that they have excellent thermal and mechanical properties. The glass transition temperatures (Tg) of cured PNBI/E51 blends were higher than 207 °C (obtained by DMA). The 5% weight loss (T5) and char yield at 800 °C (CR) were higher than 360 °C and 14% in nitrogen, respectively (obtained by TGA). Consequently, this study shows a novel modification in the method for the preparation of epoxy or phthalonitrile blend systems.
Co-reporter:Jianghuai Hu;Rui Sun;Yihao Wu;Jiangbo Lv;Zhiping Wang;Ke Zeng
RSC Advances (2011-Present) 2017 vol. 7(Issue 69) pp:43978-43986
Publication Date(Web):2017/09/07
DOI:10.1039/C7RA06162E
Binary blends composed of benzimidazole-containing phthalonitrile (PNBI) and epoxy resin E51 were prepared. The PNBI/E51 (PE) blends showed good compatibilities and unique synergistic curing behaviors on full consumption of nitrile groups (PE19, PNBI:E51 = 1 : 9 in weight ratio) and epoxy groups in the view of DSC, rheology and IR. Curing procedures of the PE blends were determined by DSC and DMA. Studies on the curing procedure showed that the PE blends exhibited good processability and could be fully cured at a temperature lower than 210 °C. Studies on the cured PE blends showed that they have excellent thermal and mechanical properties. The glass transition temperatures (Tg) of cured PNBI/E51 blends were higher than 207 °C (obtained by DMA). The 5% weight loss (T5) and char yield at 800 °C (CR) were higher than 360 °C and 14% in nitrogen, respectively (obtained by TGA). Consequently, this study shows a novel modification in the method for the preparation of epoxy or phthalonitrile blend systems.
Co-reporter:Jianghuai Hu, Zhiping Wang, Zheng Lu, Chang Chen, Meng Shi, Jianbo Wang, Erjin Zhao, Ke Zeng, Gang Yang
Polymer 2017 Volume 119(Volume 119) pp:
Publication Date(Web):16 June 2017
DOI:10.1016/j.polymer.2017.05.012
•Bio-based adenine was introduced into the mainchain of high performance polymers (polyimide) for the first time.•The obtained polyimide showed outstanding thermal and mechanical properties.•System studies indicate that the outstanding thermal and mechanical properties are related to the hydrogen-bonding interactions.Because of the unique conjugated heterocyclic structure and the presence of reactive groups, adenine which can be obtained from biomass may be an ideal bio-based alternative structure of petroleum-based aromatic/heterocyclic structures. In this paper, the adenine was introduced into mainchain of polyimide (API) for the first time to evaluate the feasibility of replacing petroleum-based aromatic/heterocyclic structures by adenine. Systematic studies showed that the API possesses outstanding solubility, thermal and mechanical properties (glass transition temperature (Tg): 363 °C, weight residual of 95%: 513 °C (N2); 506 °C (Air), tensile strength: 144 MPa). Systematic studies indicated that hydrogen-bonding interaction could be a significant cause of these unique thermal and mechanical properties.Synopsis: Adenine is an ideal bio-based alternative structure of petroleum-based aromatic/heterocyclic structures in high-performance polymers.Download high-res image (369KB)Download full-size image
Co-reporter:Jiang-bo Lv;Jing-zhi Ma;Kang Cheng;Chang Chen
Chinese Journal of Polymer Science 2017 Volume 35( Issue 12) pp:1561-1571
Publication Date(Web):16 September 2017
DOI:10.1007/s10118-017-1992-8
A series of polymer blends were prepared from 1,3-bis(3,4-dicyanophenoxy)benzene (3BOCN) and epoxy resin with methyl tetrahydrophthalic anhydride as curing agent. The curing behavior and curing kinetics of the blends were studied by differential scanning calorimetry. The apparent activation energy of the blends with various contents of 3BOCN was higher than that of the blends without 3BOCN. A model experiment suggested that there is no obvious reaction between phthalonitrile and epoxy. The thermal and mechanical properties of the polymer blends were evaluated. The polymer blends exhibit high storage modulus and char yield compared with the neat epoxy. The polymer blends show ductile fracture morphology by scanning electron microscopy (SEM) images.
Co-reporter:Ping Yuan, Suchun Ji, Jianghuai Hu, Xueping Hu, Ke Zeng, Gang Yang
Polymer 2016 Volume 102() pp:266-280
Publication Date(Web):12 October 2016
DOI:10.1016/j.polymer.2016.09.025
•Blends of alicyclic imide moiety and phthalontrile show highly efficient Thermal Synergistic Polymerization effect.•CN of the phthalonitrile could be completely and rapidly consumed, with no triazine, minor phthalocyanine and primary polyisoindolines formation.•The reaction between alicyclic imide moiety and phthalonitrile suggests a free radical process.•The cured polymers showed excellent thermal properties, low boiling water absorbance and moderate dielectric constant.Blends of phthalonitrile (CN) and alicyclic imide compounds synthesized from tetrahydrophthalic anhydride (CC), methyl tetrahydrophthalic anhydride (MCC) and hexahydrophthalic anhydride (HCC), respectively, were prepared and characterized. Results from rheological studies demonstrated the scope of a novel Thermal Synergistic Polymerization (TSP) effect between phthalonitrile and the alicyclic imide compounds. FTIR data showed a unique phenomenon, which is, the CN of the phthalonitrile compound could be completely and rapidly consumed without generating any triazine ring. Further works on cured products of CC/CN system showed comparable or even higher thermal oxidation stability, low boiling water absorbance and moderate dielectric constant (ε′ in the range of 4.8∼4.5) with almost no voids compared with that of the phthalonitrile resins promoted by traditional curing system of active hydrogen. Model system was designed to study the mechanism of TSP effect of alicyclic imide moiety/phthalonitrile. The systematic characterizations by FTIR, UV–Vis, MALDI-TOF MS, free radical scavenger (DPPH), EPR, etc. showed that the TSP reaction undergoes both copolymerization and homopolymerization with no triazine formation, involving a free radical process. Structural analysis of the oligomers suggested that phthalocyanine rings were a minor component of the thermoset networks, while polyisoindolines were the primary structural motif.
Co-reporter:Suchun Ji, Ping Yuan, Jianghuai Hu, Rui Sun, Ke Zeng, Gang Yang
Polymer 2016 Volume 84() pp:365-370
Publication Date(Web):10 February 2016
DOI:10.1016/j.polymer.2016.01.006
•A novel curing agent was designed and synthesized for phthalonitrile monomer.•The new phthalonitrile/curing agent system has great process ability and the cured polymer has excellent thermal properties.•No triazine absorption peak was observed in IR spectra of the polymer network.•Phthalocyanine and isoindoline were formed during the curing process.A novel methyl tetrahydrophthalic anhydride end-capped imide compound (MODA) was firstly used to promote the curing reaction of phthalonitrile monomer 1,3-bis(3,4-dicyanophenoxy) (3BOCN). The curing behaviors of 3BOCN/MODA blend were studied by differential scanning calorimetry (DSC) and rheological analysis, which suggested that the blend possessed a wide processing window. IR spectra exhibited no triazine has been formed in the curing process and the nitrile group absorption peak almost disappeared after post-cured, the thermogravimetric analysis (TGA) and dynamic mechanical analysis (DMA) revealed that the cured phthalonitrile resins have excellent thermal properties and high glass transition temperature (Tg).
Co-reporter:Jianbo Wang, Jianghuai Hu, Ke Zeng and Gang Yang
RSC Advances 2015 vol. 5(Issue 127) pp:105038-105046
Publication Date(Web):26 Nov 2015
DOI:10.1039/C5RA18472J
The in situ reaction of a hydroxy group with a phthalonitrile system was carried out by the simple nucleophilic displacement of a nitro-substituent from 4-nitrophthalonitrile in a dipolar aprotic solvent, in a one-pot reaction. The hydroxy-containing phthalonitrile system (HPBD) was prepared by mixing 4-hydroxyphenoxy phthalonitrile (HPPH) and 1,3-bis(3,4-dicyanophenoxy)benzene (BDB), followed by heating. The curing behavior was studied using differential scanning calorimetry and dynamic rheological analysis, and the results indicated that the HPBD exhibits a large processing window (∼75 °C) and low complex viscosity (0.1–1 Pa s) at moderate temperatures. Fourier transform infrared spectroscopy (FT-IR) showed that polytriazine, polyindoline and phthalocyanine structures were formed during polymerization, and that the introduction of HPPH facilitated the curing reaction. Additionally, the prepared HPBD polymers showed outstanding thermal stability, a high modulus and a high glass transition temperature (Tg). After curing at 300 °C, the Tg of HPBD resin was raised to 410 °C. Postcuring effects on the thermal and dynamic mechanical properties were evaluated using thermogravimetric analysis (TGA) and dynamic mechanical analysis (DMA).
Co-reporter:Jianghuai Hu, Yancui Liu, Yan Jiao, Suchun Ji, Rui Sun, Ping Yuan, Ke Zeng, Xuemei Pu and Gang Yang
RSC Advances 2015 vol. 5(Issue 21) pp:16199-16206
Publication Date(Web):23 Jan 2015
DOI:10.1039/C4RA17306F
A novel unsymmetrical phthalimide-containing phthalonitrile (PIPN) was successfully synthesized. The chemical structure of the PIPN monomer was confirmed by various spectroscopic techniques. Rheology and differential scanning calorimetry (DSC) revealed that the self-promoted curing reaction of the PIPN was an extremely sluggish process. The fully cured PIPN polymers showed excellent thermal properties revealed by thermogravimetric analysis (TGA) and DSC. IR and solid-state UV-Vis diffusion reflectance spectra confirmed the formation of the triazine and phthalocyanine ring during the curing reaction. Rheometric studies suggested that the curing reaction of phthalonitrile with a phthalimide group was faster compared to the reaction with a benzimidazole ring, and a nucleophilic addition reaction mechanism was successfully introduced to explain this phenomenon.
Co-reporter:Qi Bian;Kai Qiu;Jiaojian Liu;Yancun Niu;Yancui Liu
Macromolecular Research 2015 Volume 23( Issue 7) pp:628-635
Publication Date(Web):2015 July
DOI:10.1007/s13233-015-3090-5
Solid vinyl monomer with functional group “phthalonitrile” was successfully introduced into microspheres to make poly{styene-co-4-(4-vinylphenoxy) phthalonitrile} microspheres (PSPMs) with uniform (UPSPMs) and core-shell (core-shell PSPMs) structure using soap-free emulsion polymerization by the new approach of “codissolution”. The core-shell PSPMs then were used as the design platform to make metallophthalocyanine-containing microspheres. EA, FTIR, SEM, TEM, UV-vis, TGA, XPS, solid 1H NMR and XRD techniques were employed to analyze the formation and morphology of PSPMs and metallophthalocyanine-containing microspheres. The results showed that UPSPMs and core-shell PSPMs were both realized and they were regular sphericities with diameters of around 370 nm. The percentages of reacting weight of 4-(4-vinylphenoxy) phthalonitrile were close to 50%. Based on the design platform of core-shell PSPMs, metallophthalocyanine-containing microspheres could be obtained and the content of metallophthalocyanine was close to 19%.
Co-reporter:Jianghuai Hu;Junwei Zhang;Yun Zou;Ke Zeng
Macromolecular Research 2014 Volume 22( Issue 10) pp:1074-1083
Publication Date(Web):2014 October
DOI:10.1007/s13233-014-2158-y
Approaches to promote the post-cure reaction of polyimide with pendant phthalonitrile unit (CN-PI) were first realized by introducing of hydroxyl groups via chemical copolymerization or physical blending. The post-cure reaction of the CN-PI was performed at 250 or 300 °C, and monitored by various techniques, such as infrared spectroscopy (IR), differential scanning calorimetry (DSC), wide-angle X-ray diffraction (WAXD), scanning electron microscopy (SEM), and thermogravimetric analysis (TGA). A significant result was found in that the trend of the increasing glass transition temperature Tg with nitrile conversion followed DiBenedetto’s equation. This provided a chance to deeply discuss the relationship between molecular structure, segmental mobility, and cure behavior of CNPI. Chemical structure changes and morphology evolution of the polymer during post-cure process were investigated by IR, WAXD, and SEM. The thermal and mechanical properties of polymer films showed it to be a thermally stable and strong material.
Co-reporter:Ke Zeng;Qiao Guo;Shuai Gao;Dimeng Wu;Haojun Fan
Macromolecular Research 2012 Volume 20( Issue 1) pp:10-20
Publication Date(Web):2012 January
DOI:10.1007/s13233-012-0007-4
A series of new asymmetric biphenyl dianhydrides, 2-phenoxy(o-methylphenoxy, m-methylphenoxy, and p-methylphenoxy)-4,4,5,5-biphenyltetracarboxylic dianhydrides, was readily synthesized using a five-step route. A new symmetric biphenyl dianhydride, 2,2-di(o-methylphenoxy)-4,4,5,5-biphenyltetracarboxylic dianhydride, was also synthesized using the similar procedure. The polyimides were prepared from such new dianhydrides and commercial diamines by high-temperature one-step polymerization. The asymmetric and symmetric substituent solubility and thermal property relationships of the resulting polyimides were investigated. Interestingly, the thermally reversible sol-gel transitions were observed for the polymer solutions of the polyimides derived from those asymmetric dianhydrides and 1,4-phenylenediamine (p-PDA). Unexpectedly, the polyimides derived from asymmetric dianhydrides did not show better organosolubility than those of the homologous polyimides derived from symmetric dianhydrides. The structures of the substituents (phenoxy, o-methylphenoxy, m-methylphenoxy and p-methylphenoxy) have a significant effect on both the solubility and the thermal properties of these polyimides. The polyimides derived from asymmetric dianhydrides show enhanced thermal properties relative to the symmetric dianhydridesderived polyimides. These results can be attributed to their different degrees of molecular packing revealed by wideangle X-ray diffraction measurements.
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Co-reporter:Ke Zeng;Li Li;Shourong Xiang;Yun Zhou
Polymer Bulletin 2012 Volume 68( Issue 7) pp:1879-1888
Publication Date(Web):2012 April
DOI:10.1007/s00289-011-0663-0
New polyimides with pendant phthalonitrile units were synthesized via the conventional two-step polymerization approach. The chemical structure of the PIs was confirmed by IR and 1H NMR spectra. The thermogravimetric analysis and differential scanning calorimetry revealed that the thermal properties of the new PIs along with their solvent-resistance can be promoted after thermal treatment at 300 °C. This promotion can be attributed to the nitrile cure reaction of the phthalonitrile units indicated by the decrease in nitrile absorptions at around 2231 cm−1 of the IR spectra.
Co-reporter:Peikai Miao;Dimeng Wu;Ke Zeng;Chun'e Zhao;Guoliang Xu;Zhifu Huang
Journal of Applied Polymer Science 2011 Volume 120( Issue 1) pp:
Publication Date(Web):
DOI:10.1002/app.33174
Abstract
This article investigated the effects of electron beam (EB) irradiation on poly(D,L-lactic acid)-b-poly(ethylene glycol) copolymer (PLEG) and poly(L-lactic acid) (PLLA). The dominant effect of EB irradiation on both PLEG and PLLA was chain scission. With increasing dose, recombination reactions or partial crosslinking of PLEG can occur in addition to chain scission, but there was no obvious crosslinking for PLLA at doses below 200 kGy. The chain scission degree of irradiated PLEG and PLLA was calculated to be 0.213 and 0.403, respectively. The linear relationships were also established between the decrease in molecular weight with increasing dose. Elongation at break of the irradiated PLEG and PLLA decreased significantly, whereas the tensile strength and glass transition temperature of PLLA decreased much more significantly compared with PLEG. The presence of poly(ethylene glycol) (PEG) chain segment in PLEG was the key factor in its greater stability to EB irradiation compared with PLLA. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2011
Co-reporter:Peikai Miao, Dimeng Wu, Ke Zeng, Guoliang Xu, Chun’e Zhao, Gang Yang
Polymer Degradation and Stability 2010 Volume 95(Issue 9) pp:1665-1671
Publication Date(Web):September 2010
DOI:10.1016/j.polymdegradstab.2010.05.028
Co-reporter:Ke Zeng, Ke Zhou, Shaohong Zhou, Haibing Hong, Hongfei Zhou, Yipeng Wang, Peikai Miao, Gang Yang
European Polymer Journal 2009 Volume 45(Issue 4) pp:1328-1335
Publication Date(Web):April 2009
DOI:10.1016/j.eurpolymj.2008.12.036
A series of hydroxy-containing phthalonitrile model compounds (HPNM) with 1:1 molar ratio of hydroxy group to phthalonitrile unit were successfully synthesized. The molecular structures were identified by FTIR and 1H NMR spectroscopic techniques. The model compounds can be thermally polymerized by duration at 225 °C for various times, even in the absence of curing additives. The thermal properties of the cured products were characterized by thermogravimetric analysis. Char yields (800 °C) of the final cured products were in the range 50–73%. The 5% and 10% weight loss ranged from 320 to 420 °C and 360–490 °C, respectively. Differential scanning calorimetry and FTIR were used to monitor the cure reaction. The results reveal that cure behaviors of the HPNM are closely correlated to their molecular structures, although each HPNM has a 1:1 molar ratio of hydroxy group to phthalonitrile unit. Therefore, the thermal properties of the final cured products depend mainly on the molecular structures of the corresponding HPNM, where differences in HPNM acidities should be considered and may contribute to their different cure behaviors.
Co-reporter:Peikai Miao;Chun'e Zhao;Guoliang Xu;Qiang Fu;Wenrui Tang;Ke Zeng;Yipeng Wang;Hongfei Zhou
Journal of Applied Polymer Science 2009 Volume 112( Issue 5) pp:
Publication Date(Web):
DOI:10.1002/app.29866
Abstract
This article investigates the effects of electron beam (EB) radiation on poly(D,L-lactic acid)-b-poly (ethylene glycol) copolymer (PLA-b-PEG-b-PLA). The copolymer films were EB irradiated at doses from 0 to 100 kGy. The degradation of these films was studied by measuring the changes in their molecular weight, mechanical and thermal properties. The dominant effect of EB radiation on PLA-b-PEG-b-PLA is chain-scission. With increasing irradiation dose, recombination reactions or partial crosslinking may occur in addition to chain scission. The degree of chain scission Gs and crosslinking Gx of sample are calculated to be 0.213 and 0.043, respectively. A linear relationship is also established between the decreases in molecular weight with increasing irradiation dose. Elongation at break of the irradiated sample decreases significantly, whereas its tensile strength decreases slightly. The glass transition temperature (Tg) is basically invariant as a function of irradiation dose. Thermogravimetric analysis shows that its thermal stability decreases with increasing dose. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009
Co-reporter:Shaohong Zhou;Haibing Hong;Ke Zeng;Peikai Miao;Hongfei Zhou
Polymer Bulletin 2009 Volume 62( Issue 5) pp:
Publication Date(Web):2009 May
DOI:10.1007/s00289-009-0041-3
A new amino-containing phthalonitrile derivative 4-(4-(3, 5-diaminobenzoyl) phenoxy) phthalonitrile (DAPN) was successfully synthesized. Its structure was identified by FT-IR and 1H-NMR. DAPN can be thermally polymerized by duration at 230 °C for various times under a nitrogen atmosphere, even in the absence of curing additives. The thermal properties of the cured products were characterized by TGA and DSC. The 5 and 10% weight loss temperatures ranged from 442 to 446 and 504 to 505 °C, respectively. Char yields (800 °C) were in the range of 72.7–72.9%. DSC data showed that the melting peak of the cured products disappeared due to their thermal polymerization. The insolubility in concentrated sulfuric acid and FT-IR of the cured products indicated the formation of cross-linked networks.
Co-reporter:Ke Zeng, Haibing Hong, Shaohong Zhou, Dimeng Wu, Peikai Miao, Zhifu Huang, Gang Yang
Polymer 2009 50(21) pp: 5002-5006
Publication Date(Web):
DOI:10.1016/j.polymer.2009.08.033
![1,2-Benzenedicarbonitrile, 4-[3-[5-[[2,3-dihydro-1,3-dioxo-2-[3-(2-phenylethynyl)phenyl]-1H-isoindol-5-yl]oxy]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3784000/1637727-91-3.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[[2,3-dihydro-1,3-dioxo-2-[3-(2-phenylethynyl)phenyl]-1H-isoindol-5-yl]oxy]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3784000/1637727-91-3_b.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)oxy]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3784000/1644293-42-4.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)oxy]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3784000/1644293-42-4_b.png)
![1,2-Benzenedicarbonitrile, 4-[2-(3,5,6,7-tetrahydro-1,3,5,7-tetraoxopyrrolo[3,4-f]isoindol-2(1H)-yl)phenoxy]-](/data/chemimg/3783900/1644293-44-6.png)
![1,2-Benzenedicarbonitrile, 4-[2-(3,5,6,7-tetrahydro-1,3,5,7-tetraoxopyrrolo[3,4-f]isoindol-2(1H)-yl)phenoxy]-](/data/chemimg/3783900/1644293-44-6_b.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)carbonyl]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3783900/1644293-48-0.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)carbonyl]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3783900/1644293-48-0_b.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[1-(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3783900/1644293-50-4.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[1-(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3783900/1644293-50-4_b.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[1-(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)-1-methylethyl]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3783900/1644293-58-2.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[1-(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)-1-methylethyl]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3783900/1644293-58-2_b.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)sulfonyl]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3783900/1644293-60-6.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)sulfonyl]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3783900/1644293-60-6_b.png)
![1,2-Benzenedicarbonitrile, 4,4'-[[5-[5-[(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)oxy]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]-1,3-phenylene]bis(oxy)]bis-](/data/chemimg/3783900/1644293-62-8.png)
![1,2-Benzenedicarbonitrile, 4,4'-[[5-[5-[(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)oxy]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]-1,3-phenylene]bis(oxy)]bis-](/data/chemimg/3783900/1644293-62-8_b.png)
![1,2-Benzenedicarbonitrile, 4,4'-[[2-(3,5,6,7-tetrahydro-1,3,5,7-tetraoxobenzo[1,2-c:4,5-c']dipyrrol-2(1H)-yl)-1,3-phenylene]bis(oxy)]bis-](/data/chemimg/3783900/1644293-64-0.png)
![1,2-Benzenedicarbonitrile, 4,4'-[[2-(3,5,6,7-tetrahydro-1,3,5,7-tetraoxobenzo[1,2-c:4,5-c']dipyrrol-2(1H)-yl)-1,3-phenylene]bis(oxy)]bis-](/data/chemimg/3783900/1644293-64-0_b.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[[2-[4-(1H-benzimidazol-2-yl)phenyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl]oxy]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3783900/1671091-62-5.png)
![1,2-Benzenedicarbonitrile, 4-[3-[5-[[2-[4-(1H-benzimidazol-2-yl)phenyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl]oxy]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl]phenoxy]-](/data/chemimg/3783900/1671091-62-5_b.png)
![Pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrone, 2,6-di-9H-purin-6-yl-](/data/chemimg/3783900/1826861-82-8.png)
![Pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrone, 2,6-di-9H-purin-6-yl-](/data/chemimg/3783900/1826861-82-8_b.png)
![[5,5'-Bi-1H-isoindole]-1,1',3,3'(2H,2'H)-tetrone, 2,2'-bis(hexahydro-2,6-dioxo-4-pyrimidinyl)-](/data/chemimg/3783900/1826861-90-8.png)
![[5,5'-Bi-1H-isoindole]-1,1',3,3'(2H,2'H)-tetrone, 2,2'-bis(hexahydro-2,6-dioxo-4-pyrimidinyl)-](/data/chemimg/3783900/1826861-90-8_b.png)
![Pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrone, 2,6-bis(1,2-dihydro-1-oxo-6-isoquinolinyl)-](/data/chemimg/3783900/1826861-93-1.png)
![Pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrone, 2,6-bis(1,2-dihydro-1-oxo-6-isoquinolinyl)-](/data/chemimg/3783900/1826861-93-1_b.png)
![[5,5'-Bi-1H-isoindole]-1,1',3,3'(2H,2'H)-tetrone, 2,2'-di-7H-pyrrolo[2,3-d]pyrimidin-4-yl-](/data/chemimg/3783900/1826861-95-3.png)
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