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Chemistry
Organic Building Blocks
Benzene Compounds
N,N'-(4,5-Dicyano-1,2-phenylene)bis(4-methylbenzenesulfonamide)
Chemistry
Material Science
Organic Building Blocks
Organic monomer of COF Organic ligands for MOF materials
Benzene Compounds
Cyano COF monomer Other MOF ligands

[ CAS No. 854663-68-6 ]

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Chemical Structure| 854663-68-6
Chemical Structure| 854663-68-6
Structure of 854663-68-6 * Storage: {[proInfo.prStorage]}

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Product Details of [ 854663-68-6 ]

CAS No. :854663-68-6 MDL No. :MFCD34469795
Formula : C22H18N4O4S2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :466.53 g/mol Pubchem ID :-
Synonyms :

Safety of [ 854663-68-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 854663-68-6 ]

  • Downstream synthetic route of [ 854663-68-6 ]

[ 854663-68-6 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 88617-67-8 ]
  • [ 544-92-3 ]
  • [ 854663-68-6 ]
YieldReaction ConditionsOperation in experiment
34% In N,N-dimethyl-formamide at 140℃; for 20h;
Reference： [1]Yueksel, Fatma; Guerek, Ayse Guel; Lebrun, Colette; Ahsen, Vefa [New Journal of Chemistry, 2005, vol. 29, # 5, p. 726 - 732]
  • 2
  • [ 854663-68-6 ]
  • 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: N,N'-(4,5-dicyano-1,2-phenylene)bis(4-methylbenzenesulfonamide) With octanol; pentan-1-ol; magnesium at 185℃; for 18h; Stage #2: With trifluoroacetic acid In tetrahydrofuran at 50℃; for 5h;
5.5% With lithium In pentan-1-ol for 60h; Heating;
Reference： [1]Meng, Zheng; Luo, Jianmin; Li, Weiyang; Mirica, Katherine A. [Journal of the American Chemical Society, 2020, vol. 142, # 52, p. 21656 - 21669]
[2]Yueksel, Fatma; Guerek, Ayse Guel; Lebrun, Colette; Ahsen, Vefa [New Journal of Chemistry, 2005, vol. 29, # 5, p. 726 - 732]
  • 3
  • [ 854663-68-6 ]
  • octatosylamido phthalocyanato zinc(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With zinc diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol for 18h; Heating;
Reference： [1]Yueksel, Fatma; Guerek, Ayse Guel; Lebrun, Colette; Ahsen, Vefa [New Journal of Chemistry, 2005, vol. 29, # 5, p. 726 - 732]
  • 4
  • [ 854663-68-6 ]
  • octatosylamido phthalocyanato nickel(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With 1,8-diazabicyclo[5.4.0]undec-7-ene; nickel dichloride In hexan-1-ol for 18h; Heating;
Reference： [1]Yueksel, Fatma; Guerek, Ayse Guel; Lebrun, Colette; Ahsen, Vefa [New Journal of Chemistry, 2005, vol. 29, # 5, p. 726 - 732]
  • 5
  • [ 557-34-6 ]
  • [ 854663-68-6 ]
  • octatosylamido phthalocyaninato zinc(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With 8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) In further solvent(s) a mixt. of a ligand (4.00 mmol), Zn-contg. compd. (4.00 mmol), DBU (6.0 mmol) and n-hexanol was heated to reflux for 18 h under Ar; solvent was removed under reduced pressure; complex was washed with C2H5OH and dissolved in acetic acid-CH2Cl2 (1:5); extn. with distd. water; org. soln. was dried over anhyd. Na2SO4 and concd.; purifn. over silica gel (CH2Cl2 as eluent); elem. anal.;
Reference： [1]Yueksel, Fatma; Guerek, Ayse Guel; Lebrun, Colette; Ahsen, Vefa [New Journal of Chemistry, 2005, vol. 29, # 5, p. 726 - 732]
  • 6
  • nickel dichloride [ No CAS ]
  • [ 854663-68-6 ]
  • octatosylamido phthalocyaninato nickel(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With 8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) In further solvent(s) a mixt. of a ligand (4.00 mmol), Ni-contg. compd. (4.00 mmol), DBU (6.0 mmol) and n-hexanol was heated to reflux for 18 h under Ar; solvent was removed under reduced pressure; complex was washed with C2H5OH and dissolved in acetic acid-CH2Cl2 (1:5); extn. with distd. water; org. soln. was dried over anhyd. Na2SO4 and concd.; purifn. over silica gel (CH2Cl2 as eluent); elem. anal.;
Reference： [1]Yueksel, Fatma; Guerek, Ayse Guel; Lebrun, Colette; Ahsen, Vefa [New Journal of Chemistry, 2005, vol. 29, # 5, p. 726 - 732]
  • 7
  • [ 156903-56-9 ]
  • nickel dichloride [ No CAS ]
  • [ 854663-68-6 ]
  • [ 954371-14-3 ]
YieldReaction ConditionsOperation in experiment
8% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) 2 equiv. of thio-compd. and 1 equiv. of the amine were refluxed with 1.5equiv. of NiCl2 and 3 equiv. of DBU for 18 h under Ar; cooling to room temp., treatment with EtOH, filtering, washing several times with EtOH, thin layer chromy. (5:2 CH2Cl2:n-hexane), elem. anal.;
Reference： [1]Yuksel, Fatma; Atilla, Devrim; Ahsen, Vefa [Polyhedron, 2007, vol. 26, # 15, p. 4551 - 4556]
  • 8
  • [ 156903-57-0 ]
  • nickel dichloride [ No CAS ]
  • [ 854663-68-6 ]
  • [ 954371-16-5 ]
YieldReaction ConditionsOperation in experiment
7% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) 2 equiv. of thio-compd. and 1 equiv. of the amine were refluxed with 1.5equiv. of NiCl2 and 3 equiv. of DBU for 18 h under Ar; cooling to room temp., treatment with EtOH, filtering, washing several times with EtOH, thin layer chromy. (5:1 CH2Cl2:n-hexane), elem. anal.;
Reference： [1]Yuksel, Fatma; Atilla, Devrim; Ahsen, Vefa [Polyhedron, 2007, vol. 26, # 15, p. 4551 - 4556]
  • 9
  • nickel dichloride [ No CAS ]
  • [ 298694-11-8 ]
  • [ 854663-68-6 ]
  • [ 954371-18-7 ]
YieldReaction ConditionsOperation in experiment
6% With 1,8-diazabicyclo[5.4.0]undec-7-ene In further solvent(s) 2 equiv. of thio-compd. and 1 equiv. of the amine were refluxed with 1.5equiv. of NiCl2 and 3 equiv. of DBU for 18 h under Ar; cooling to room temp., treatment with EtOH, filtering, washing several times with EtOH, thin layer chromy. (5:1 CH2Cl2:n-hexane), elem. anal.;
Reference： [1]Yuksel, Fatma; Atilla, Devrim; Ahsen, Vefa [Polyhedron, 2007, vol. 26, # 15, p. 4551 - 4556]
  • 10
  • [ 114364-56-6 ]
  • [ 854663-68-6 ]
  • C118H175N10O10S2Zn [ No CAS ]
YieldReaction ConditionsOperation in experiment
13.8% With zinc diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In pentan-1-ol for 18h; Reflux; Inert atmosphere;
Reference： [1]Location in patent: experimental part Pur, Bilge; Yuksel, Fatma; Ahsen, Vefa [Dyes and Pigments, 2012, vol. 93, # 1-3, p. 1498 - 1505]
  • 11
  • [ 49633-28-5 ]
  • [ 854663-68-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; sodium acetate; bromine / 1 h / 100 °C 2: N,N-dimethyl-formamide / 20 h / 120 °C
Reference： [1]Thelemann, Jonas; Illarionov, Boris; Barylyuk, Konstantin; Geist, Julie; Kirchmair, Johannes; Schneider, Petra; Anthore, Lucile; Root, Katharina; Trapp, Nils; Bacher, Adelbert; Witschel, Matthias; Zenobi, Renato; Fischer, Markus; Schneider, Gisbert; Diederich, François [ChemMedChem, 2015, vol. 10, # 12, p. 2090 - 2098]
  • 12
  • [ 88617-67-8 ]
  • copper(l) cyanide [ No CAS ]
  • [ 854663-68-6 ]
YieldReaction ConditionsOperation in experiment
69% In N,N-dimethyl-formamide at 120℃; for 48h; Inert atmosphere;
30% In N,N-dimethyl-formamide at 120℃; for 20h;
22% In N,N-dimethyl-formamide Inert atmosphere;
In N,N-dimethyl-formamide
In N,N-dimethyl-formamide at 110℃; for 12h;

Reference： [1]Meng, Zheng; Stolz, Robert M.; Mirica, Katherine A. [Journal of the American Chemical Society, 2019, vol. 141, # 30, p. 11929 - 11937]
[2]Thelemann, Jonas; Illarionov, Boris; Barylyuk, Konstantin; Geist, Julie; Kirchmair, Johannes; Schneider, Petra; Anthore, Lucile; Root, Katharina; Trapp, Nils; Bacher, Adelbert; Witschel, Matthias; Zenobi, Renato; Fischer, Markus; Schneider, Gisbert; Diederich, François [ChemMedChem, 2015, vol. 10, # 12, p. 2090 - 2098]
[3]Huang, Ning; Irle, Stefan; Jiang, Donglin; Jiang, Qiuhong; Lee, Ka Hung; Xu, Xiaoyi; Yue, Yan [Angewandte Chemie - International Edition, 2020, vol. 59, # 38, p. 16587 - 16593][Angew. Chem., 2020, vol. 132, # 38, p. 16730 - 16736,7]
[4]Jia, Hongxing; Yao, Yuchuan; Zhao, Jiangtao; Gao, Yuyue; Luo, Zhenlin; Du, Pingwu [Journal of Materials Chemistry A, 2018, vol. 6, # 3, p. 1188 - 1195]
[5]Yue, Yan; Cai, Peiyu; Xu, Xiaoyi; Li, Hanying; Chen, Hongzheng; Zhou, Hong-Cai; Huang, Ning [Angewandte Chemie - International Edition, 2021, vol. 60, # 19, p. 10806 - 10813][Angew. Chem., 2021, vol. 133, # 19, p. 10901 - 10908,8]
  • 13
  • [ 95-54-5 ]
  • [ 854663-68-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 12 h 2: acetic acid; sodium acetate; bromine / 1 h / 100 °C 3: N,N-dimethyl-formamide / 20 h / 120 °C
Multi-step reaction with 3 steps 1: pyridine 2: acetic acid; bromine 3: N,N-dimethyl-formamide
Multi-step reaction with 3 steps 1: pyridine / 12 h 2: bromine; sodium acetate; acetic acid / Reflux 3: N,N-dimethyl-formamide / 48 h / 120 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: pyridine / N,N-dimethyl-formamide / 12 h 2: bromine; acetic acid / 6 h 3: N,N-dimethyl-formamide / Inert atmosphere
Multi-step reaction with 3 steps 1: pyridine / N,N-dimethyl-formamide / 12 h / 80 °C 2: bromine; acetic acid / 6 h / 20 °C 3: N,N-dimethyl-formamide / 12 h / 110 °C

Reference： [1]Thelemann, Jonas; Illarionov, Boris; Barylyuk, Konstantin; Geist, Julie; Kirchmair, Johannes; Schneider, Petra; Anthore, Lucile; Root, Katharina; Trapp, Nils; Bacher, Adelbert; Witschel, Matthias; Zenobi, Renato; Fischer, Markus; Schneider, Gisbert; Diederich, François [ChemMedChem, 2015, vol. 10, # 12, p. 2090 - 2098]
[2]Jia, Hongxing; Yao, Yuchuan; Zhao, Jiangtao; Gao, Yuyue; Luo, Zhenlin; Du, Pingwu [Journal of Materials Chemistry A, 2018, vol. 6, # 3, p. 1188 - 1195]
[3]Meng, Zheng; Stolz, Robert M.; Mirica, Katherine A. [Journal of the American Chemical Society, 2019, vol. 141, # 30, p. 11929 - 11937]
[4]Huang, Ning; Irle, Stefan; Jiang, Donglin; Jiang, Qiuhong; Lee, Ka Hung; Xu, Xiaoyi; Yue, Yan [Angewandte Chemie - International Edition, 2020, vol. 59, # 38, p. 16587 - 16593][Angew. Chem., 2020, vol. 132, # 38, p. 16730 - 16736,7]
[5]Yue, Yan; Cai, Peiyu; Xu, Xiaoyi; Li, Hanying; Chen, Hongzheng; Zhou, Hong-Cai; Huang, Ning [Angewandte Chemie - International Edition, 2021, vol. 60, # 19, p. 10806 - 10813][Angew. Chem., 2021, vol. 133, # 19, p. 10901 - 10908,8]
  • 14
  • [ 98-59-9 ]
  • [ 854663-68-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 12 h 2: acetic acid; sodium acetate; bromine / 1 h / 100 °C 3: N,N-dimethyl-formamide / 20 h / 120 °C
Multi-step reaction with 3 steps 1: pyridine 2: acetic acid; bromine 3: N,N-dimethyl-formamide
Multi-step reaction with 3 steps 1: pyridine / 12 h 2: bromine; sodium acetate; acetic acid / Reflux 3: N,N-dimethyl-formamide / 48 h / 120 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: pyridine / N,N-dimethyl-formamide / 12 h 2: bromine; acetic acid / 6 h 3: N,N-dimethyl-formamide / Inert atmosphere
Multi-step reaction with 3 steps 1: pyridine / N,N-dimethyl-formamide / 12 h / 80 °C 2: bromine; acetic acid / 6 h / 20 °C 3: N,N-dimethyl-formamide / 12 h / 110 °C

Reference： [1]Thelemann, Jonas; Illarionov, Boris; Barylyuk, Konstantin; Geist, Julie; Kirchmair, Johannes; Schneider, Petra; Anthore, Lucile; Root, Katharina; Trapp, Nils; Bacher, Adelbert; Witschel, Matthias; Zenobi, Renato; Fischer, Markus; Schneider, Gisbert; Diederich, François [ChemMedChem, 2015, vol. 10, # 12, p. 2090 - 2098]
[2]Jia, Hongxing; Yao, Yuchuan; Zhao, Jiangtao; Gao, Yuyue; Luo, Zhenlin; Du, Pingwu [Journal of Materials Chemistry A, 2018, vol. 6, # 3, p. 1188 - 1195]
[3]Meng, Zheng; Stolz, Robert M.; Mirica, Katherine A. [Journal of the American Chemical Society, 2019, vol. 141, # 30, p. 11929 - 11937]
[4]Huang, Ning; Irle, Stefan; Jiang, Donglin; Jiang, Qiuhong; Lee, Ka Hung; Xu, Xiaoyi; Yue, Yan [Angewandte Chemie - International Edition, 2020, vol. 59, # 38, p. 16587 - 16593][Angew. Chem., 2020, vol. 132, # 38, p. 16730 - 16736,7]
[5]Yue, Yan; Cai, Peiyu; Xu, Xiaoyi; Li, Hanying; Chen, Hongzheng; Zhou, Hong-Cai; Huang, Ning [Angewandte Chemie - International Edition, 2021, vol. 60, # 19, p. 10806 - 10813][Angew. Chem., 2021, vol. 133, # 19, p. 10901 - 10908,8]
  • 15
  • nickel dichloride [ No CAS ]
  • [ 854663-68-6 ]
  • 2,3,9,10,16,17,23,24-octakis(tosylamido)phthalocyaninatonickel(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 160℃; for 36h; Inert atmosphere;
28% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 200℃; for 20h; Inert atmosphere;
Reference： [1]Jia, Hongxing; Yao, Yuchuan; Zhao, Jiangtao; Gao, Yuyue; Luo, Zhenlin; Du, Pingwu [Journal of Materials Chemistry A, 2018, vol. 6, # 3, p. 1188 - 1195]
[2]Yue, Yan; Cai, Peiyu; Xu, Xiaoyi; Li, Hanying; Chen, Hongzheng; Zhou, Hong-Cai; Huang, Ning [Angewandte Chemie - International Edition, 2021, vol. 60, # 19, p. 10806 - 10813][Angew. Chem., 2021, vol. 133, # 19, p. 10901 - 10908,8]
  • 16
  • nickel dichloride [ No CAS ]
  • [ 854663-68-6 ]
  • 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Ni(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 160℃; for 36h; Inert atmosphere;
Reference： [1]Meng, Zheng; Stolz, Robert M.; Mirica, Katherine A. [Journal of the American Chemical Society, 2019, vol. 141, # 30, p. 11929 - 11937]
  • 17
  • [ 7646-79-9 ]
  • [ 854663-68-6 ]
  • octatosylamido phthalocyaninato cobalt(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 200℃; for 24h; Inert atmosphere;
Reference： [1]Huang, Ning; Irle, Stefan; Jiang, Donglin; Jiang, Qiuhong; Lee, Ka Hung; Xu, Xiaoyi; Yue, Yan [Angewandte Chemie - International Edition, 2020, vol. 59, # 38, p. 16587 - 16593][Angew. Chem., 2020, vol. 132, # 38, p. 16730 - 16736,7]
  • 18
  • iron(II) chloride [ No CAS ]
  • [ 854663-68-6 ]
  • 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Fe(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 170℃; Inert atmosphere; Sealed tube; 2.1 Synthesis of 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Fe(II) (FePc-NHTs). The synthesis of the 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Ni(II) was adapted from the literature. To a suspension of 1.00 g (2.1 mmol) of N,N′-(4,5-dicyano-1,2-phenylene)bis(4-methylbenzenesulfonamide) and 1.12 g of anhydrous FeCl2(2.1 mmol, 1.0 eq) in n-hexanol (3 mL) in a glass pressure vessel, 2 mL of DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) was added. The system was purged with N2for 10 minutes and then sealed. The reaction vessel was then heated at 170° C. for 36 hours. The reaction was then allowed to cool to room temperature. Once at room temperature, the reaction mixture was dissolved in 150 mL of a mixed solvent system of acetic acid and CH2Cl2(v/v=1:5). The organic extract was washed with water (200 mL×3) and then evaporated to dryness to provide an emerald-colored oil. The residual hexanol remaining in the oil was removed by repeatedly dispersing in 40 mL of a mixture CH2Cl2/petroleum ethers (v/v=1:3) and decanting the brownish solvent. The emerald-colored crude product was dissolved in CH2Cl2and pyridine and filtered through a fine fitted funnel. The organic mother liquor was evaporated to dryness and re-dissolved in 20 mL MeOH. The pyridine was quenched with conc. HCl (3 mL). Upon addition of HCl a solid was observed to crash out of solution. Filtration produced a fine black powder and a brown-green mother liquor. The solids were further purified by column chromatography (silica gel, eluent: CH2Cl2/MeOH/pyridine=50/2.5/0.2) to give product FePc-NHTs as a green solid (250 mg, yield 67%).1H-NMR (500 MHz, dimethyl sulfoxide (DMSO)-D6) no proton peaks were observed in low-field NMR experiments.HRMS(ES+): calculated for C88H72FeN16O16S81921.97 [M+], 960.98 [M2+]; found 1921.26 M/z, 961.63 m/z.FIG. 8illustrates high resolution mass spectroscopy analysis of FePc-NHTs. Electro-spray ionization was used in conjunction with TOF MS. The monomer ionized as m/z where z=1 or 2, and the mass of the parent peak was 1921.25 g/mol.
Reference： [1]Current Patent Assignee: DARTMOUTH COLLEGE - US2020/361976, 2020, A1 Location in patent: Paragraph 0122-0126
  • 19
  • [ 7646-79-9 ]
  • [ 854663-68-6 ]
  • 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Co(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 175℃; for 60h; Inert atmosphere; Sealed tube; 2.1 Synthesis of 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Co(II) (CoPc-NHTs). To a suspension of 4.67 g (10 mmol) of N,N′-(4,5-dicyano-1,2-phenylene)bis(4-methylbenzenesulfonamide) and 1.29 g of anhydrous CoCl2(10 mol, 1.0 eq) in n-hexanol (15 mL) in a glass pressure vessel, 5 mL of DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) was added. The system was purged with N2for 10 minutes and then sealed. The reaction vessel was then heated at 175° C. under N2for 60 hours. Upon cooling to room temperature, the reaction mixture was dissolved in 500 mL mixed solvent of acetic acid and CH2Cl2(v/v=1:5). The organic extract was washed with water (300 mL×3) and then evaporated to dryness to generate a blue solid. The residual high boiling point hexanol remaining in the solid was removed by repeatedly dispersing the solid in 40 mL of CH2Cl2/petroleum ether mixture (v/v=1:3) and decanting the brownish solvent. The blue crude product was passed through a silica gel pad (eluent: CH2Cl2→CH2Cl2/MeOH=100/1) to give as a blue solid, which was further recrystallized in a 100 mL MeOH/CH2Cl2mixture (v/v=2:1) to produce dark blue crystals (1.97 g, yield 41%).1H NMR (600 MHz, 298K, deuterated chloroform (CDCl3)) δ=10.56 (s, 4H), 9.91 (s, 4H), 9.81 (s, 4H), 9.36 (s, 4H), 9.07 (d, J=7.9 Hz, 8H), 8.41 (d, J=7.9 Hz, 8H), 7.40 (d, J=7.7 Hz, 7H), 6.61 (d, J=7.7 Hz, 8H), 3.31 (s, 12H), 1.98 (s, 12H).13C NMR (150 MHz, 298 K, CDCl3) δ=146.65, 144.01, 138.11, 136.39, 135.37, 133.20, 131.72, 129.63, 128.19, 127.35, 123.79, 122.46, 22.87, 21.51.HRMS(ESI): m/z calcd for C88H73CoNi6O16S8: 1924.2488; found: 1924.2495 [M+H]+.FIG. 9illustrates1H NMR (600 M, 298 K, CDCl3) spectrum of CoPc-NHTs andFIG. 10illustrates13C NMR (150 M, 298 K, CDCl3) spectrum of CoPc-NHTs.
Reference： [1]Current Patent Assignee: DARTMOUTH COLLEGE - US2020/361976, 2020, A1 Location in patent: Paragraph 0122; 0129-0133
  • 20
  • [ 142-71-2 ]
  • [ 854663-68-6 ]
  • 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Cu(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.26% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol at 180℃; Inert atmosphere; Sealed tube; 2.1 Synthesis of 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Cu(II) (CuPc-NHTs). The synthesis of the 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine Cu(II) was adapted from the literature. To a suspension of 1.050 g (2 mmol) of N,N′-(4,5-dicyano-1,2-phenylene)bis(4-methylbenzenesulfonamide) and 0.122 g of Cu(OAc)2(0.674 mmol, 0.3 eq) in a glass pressure vessel, 5 mL of n-hexanol was added. The system was purged with N2for 10 minutes and then sealed. The reaction vessel was heated at 180° C. for 36 hours. The reaction was then allowed to cool to room temperature. Once at room temperature, the reaction mixture was dissolved in 66 mL of a mixed solvent system of acetic acid and CH2Cl2(v/v=1:10). The organic extract was washed with water (50 mL×3) and then evaporated to dryness to provide an emerald-colored oil. The residual hexanol remaining in the oil was removed by repeatedly dispersing in 154 mL of a mixture CH2Cl2/petroleum ethers (v/v=1:10) and decanting the brownish solvent. The solids were further purified by column chromatography (silica gel, eluent: CH2Cl2/MeOH=19/1). The solids were further purified by recrystallization in a CH2Cl2/MeOH mixture (v/v=3:1) to give a blue solid (35.3 mg, yield 3.26%).1H-NMR (500 MHz, CDCl3) no proton peaks were observed in low-field NMR experiments.HRMS(ES+) calculated for C88H72CuN16O16S81928.24 [M+]; found 1930.24 m/z.FIG. 12illustrates high resolution mass spectroscopy analysis of CuPc-NHTs. Electro-spray ionization was used in conjunction with TOF MS. The monomer ionized as M/1, and the mass of the parent peak was 1930.24 g/mol.
Reference： [1]Current Patent Assignee: DARTMOUTH COLLEGE - US2020/361976, 2020, A1 Location in patent: Paragraph 122; 0137-0141
  • 21
  • [ 7646-79-9 ]
  • [ 854663-68-6 ]
  • 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine cobalt(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol for 60h; Inert atmosphere;
Reference： [1]Meng, Zheng; Luo, Jianmin; Li, Weiyang; Mirica, Katherine A. [Journal of the American Chemical Society, 2020, vol. 142, # 52, p. 21656 - 21669]
  • 22
  • nickel dichloride [ No CAS ]
  • [ 854663-68-6 ]
  • 2,3,9,10,16,17,23,24-octatosylaminophthalocyanine nickel(II) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexan-1-ol for 60h; Inert atmosphere;
Reference： [1]Meng, Zheng; Luo, Jianmin; Li, Weiyang; Mirica, Katherine A. [Journal of the American Chemical Society, 2020, vol. 142, # 52, p. 21656 - 21669]

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