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Synthesis evidence

Highly Conductive 2D Metal-Organic Framework Thin Film Fabricated by Liquid-Liquid Interfacial Reaction Using One-Pot-Synthesized Benzenehexathiol

Chen I.-F., Lu C.-F., Su W.-F. · Langmuir · 2018 · 15754-15762

10 structured synthesis routes

Completeness describes how fully the route could be reconstructed from the main article and supporting information.

Complete recipeSource: Main

Route 1: Other

15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2 · Figure 2

Metal precursorsAgNO3
Linker precursorsBHT
Solventsmethanol
Atmosphereambient/not specified
Temperatureroom temperature/not specified
Timeimmediate precipitation
Work-upparticles filtered, washed with water and acetone, dried under vacuum, pressed into 7 mm disk at 50 psi
Activationvacuum drying
Show 3 structured reagent records
RoleReagentAmount / concentrationSource
LinkerBHT10 mg, 0.037 mmol15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2 · Figure 2
Metal SourceAgNO30.1 mmol15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2 · Figure 2
Solventmethanol30 mL15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2 · Figure 2
Complete recipeSource: Main

Route 2: Liquid Liquid Interface

15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2 · Figure 1

Metal precursorsAgNO3
Linker precursorsBHT
Solvents5 mM NaOH aqueous solution; acetonitrile/ethyl acetate co-solvent v/v = 1:4
AdditivesNaOH base
Atmosphereambient/not specified
Temperatureroom temperature/not specified
Time0.5
Substrate orientationsilicon wafer covered with 300 nm silicon oxide placed in dish in advance
Work-upliquid removed slowly by syringe to deposit MOF thin film on substrate
Scalability contextAuthors note precursor concentration must be between about 0.015% and 0.1% to observe stable thin films.
Show 4 structured reagent records
RoleReagentAmount / concentrationSource
LinkerBHT5 mg, 0.0185 mmol15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2 · Figure 1
Basesodium hydroxide aqueous solution10 mL · 5 mM15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2 · Figure 1
Metal SourceAgNO30.025 mmol15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2 · Figure 1
Solventacetonitrile and ethyl acetate co-solvent10 mL + 5 mL clean co-solvent cover layer · v/v = 1:415757 and 15761 · Formation of Ag3BHT2 and Au3BHT2 · Figure 1
Complete recipeSource: Main

Route 3: Other

15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2

Metal precursorsHAuCl4
Linker precursorsBHT
Solventsmethanol
Atmosphereambient/not specified
Temperature50
Time0.5
Work-upparticles filtered, washed with water and acetone, dried under vacuum, pressed into 7 mm disk at 50 psi
Activationvacuum drying
Show 3 structured reagent records
RoleReagentAmount / concentrationSource
LinkerBHT10 mg, 0.037 mmol15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2
Metal SourceHAuCl40.1 mmol15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2
Solventmethanol30 mL15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2
Complete recipeSource: Main

Route 4: Liquid Liquid Interface

15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2

Metal precursorsHAuCl4
Linker precursorsBHT
Solvents5 mM NaOH aqueous solution; acetonitrile/ethyl acetate co-solvent v/v = 1:4
AdditivesNaOH base
Atmosphereambient/not specified
Temperatureroom temperature/not specified
Time6.5
Substrate orientationsilicon wafer covered with 300 nm silicon oxide placed in dish in advance
Work-upliquid removed slowly by syringe to deposit MOF thin film on substrate
Scalability contextAuthors note precursor concentration must be between about 0.015% and 0.1% to observe stable thin films.
Show 4 structured reagent records
RoleReagentAmount / concentrationSource
LinkerBHT5 mg, 0.0185 mmol15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2
Basesodium hydroxide aqueous solution10 mL · 5 mM15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2
Metal SourceHAuCl40.025 mmol15757 and 15761 · Formation of Ag3BHT2 and Au3BHT2
Solventacetonitrile and ethyl acetate co-solvent10 mL + 5 mL clean co-solvent cover layer · v/v = 1:415757 and 15761 · Formation of Ag3BHT2 and Au3BHT2
Partial recipeSource: Main

Route 5: Other

15755 · Results and Discussion - Synthesis of BHT · Table 1

Metal precursorsnone
Linker precursorshexafluorobenzene (C6F6); sodium methylthiolate (CH3-SNa)
Solvents1,3-dimethyl-2-imidazolidinone (DMEU)
Additivessodium particles; hydrochloric acid workup
Atmospherenitrogen
Temperature0
Time31
Oxidant / reductantsodium particles used to stabilise benzenehexathiolate anions
Work-uppoured into hydrochloric acid; precipitate filtered and washed with water and acetone
Show 5 structured reagent records
RoleReagentAmount / concentrationSource
LinkerC6F614 mmol in general method15755 · Results and Discussion - Synthesis of BHT · Table 1
AdditiveCH3-SNa0.21 mol in general method15755 · Results and Discussion - Synthesis of BHT · Table 1
SolventDMEU30 mL15755 · Results and Discussion - Synthesis of BHT · Table 1
Reductantsodium particles0.644 g, 28 mmol15755 · Results and Discussion - Synthesis of BHT · Table 1
Acidhydrochloric acid150 mL · 1.0 M15755 · Results and Discussion - Synthesis of BHT · Table 1
Partial recipeSource: Main

Route 6: Other

15755 · Results and Discussion - Synthesis of BHT · Table 1

Metal precursorsnone
Linker precursorshexafluorobenzene (C6F6); sodium ethylthiolate (C2H5-SNa)
Solvents1,3-dimethyl-2-imidazolidinone (DMEU)
Additivessodium particles; hydrochloric acid workup
Atmospherenitrogen
Temperature0
Time18
Oxidant / reductantsodium particles used to stabilise benzenehexathiolate anions
Work-uppoured into hydrochloric acid; precipitate filtered and washed with water and acetone
Show 5 structured reagent records
RoleReagentAmount / concentrationSource
LinkerC6F614 mmol in general method15755 · Results and Discussion - Synthesis of BHT · Table 1
AdditiveC2H5-SNa0.21 mol in general method15755 · Results and Discussion - Synthesis of BHT · Table 1
SolventDMEU30 mL15755 · Results and Discussion - Synthesis of BHT · Table 1
Reductantsodium particles0.644 g, 28 mmol15755 · Results and Discussion - Synthesis of BHT · Table 1
Acidhydrochloric acid150 mL · 1.0 M15755 · Results and Discussion - Synthesis of BHT · Table 1
Complete recipeSource: Main

Route 7: Other

15755 and 15760 · Table 1; Experimental Methods - Synthesis of Benzenehexathiol · Table 1

Metal precursorsnone
Linker precursorshexafluorobenzene (C6F6); sodium isopropylthiolate (i-C3H7-SNa)
Solvents1,3-dimethyl-2-imidazolidinone (DMEU)
Additivessodium particles; methanol; water; hydrochloric acid
Atmospherenitrogen
Temperature0 for first step; then 100 after sodium addition
Time6
Oxidant / reductantsodium particles used to stabilise benzenehexathiolate anions
Work-upmethanol and water injected; solution poured slowly into 1.0 M HCl; yellow solid filtered and washed with water and acetone
Scalability contextReported isolated product 3.215 g, 85% yield.
Show 7 structured reagent records
RoleReagentAmount / concentrationSource
Linkerhexahalogenobenzene / C6F614 mmol15755 and 15760 · Table 1; Experimental Methods - Synthesis of Benzenehexathiol · Table 1
Additivesodium isopropylthiolate (i-C3H7-SNa)0.21 mol15755 and 15760 · Table 1; Experimental Methods - Synthesis of Benzenehexathiol · Table 1
Solvent1,3-dimethyl-2-imidazolidinone (DMEU)30 mL15755 and 15760 · Table 1; Experimental Methods - Synthesis of Benzenehexathiol · Table 1
Reductantsodium particles0.644 g, 28 mmol15755 and 15760 · Table 1; Experimental Methods - Synthesis of Benzenehexathiol · Table 1
Solventmethanol30 mL15755 and 15760 · Table 1; Experimental Methods - Synthesis of Benzenehexathiol · Table 1
Solventwater30 mL15755 and 15760 · Table 1; Experimental Methods - Synthesis of Benzenehexathiol · Table 1
Acidhydrochloric acid150 mL · 1.0 M15755 and 15760 · Table 1; Experimental Methods - Synthesis of Benzenehexathiol · Table 1
Partial recipeSource: Main

Route 8: Other

15755 · Results and Discussion - Synthesis of BHT · Table 1

Metal precursorsnone
Linker precursorshexabromobenzene (C6Br6); sodium methylthiolate (CH3-SNa)
Solvents1,3-dimethyl-2-imidazolidinone (DMEU)
Additivessodium particles; hydrochloric acid workup
Atmospherenitrogen
Temperature100
Time72
Oxidant / reductantsodium particles used to stabilise benzenehexathiolate anions
Work-uppoured into hydrochloric acid; precipitate filtered and washed with water and acetone
Show 5 structured reagent records
RoleReagentAmount / concentrationSource
LinkerC6Br614 mmol in general method15755 · Results and Discussion - Synthesis of BHT · Table 1
AdditiveCH3-SNa0.21 mol in general method15755 · Results and Discussion - Synthesis of BHT · Table 1
SolventDMEU30 mL15755 · Results and Discussion - Synthesis of BHT · Table 1
Reductantsodium particles0.644 g, 28 mmol15755 · Results and Discussion - Synthesis of BHT · Table 1
Acidhydrochloric acid150 mL · 1.0 M15755 · Results and Discussion - Synthesis of BHT · Table 1
Partial recipeSource: Main

Route 9: Other

15755 · Results and Discussion - Synthesis of BHT · Table 1

Metal precursorsnone
Linker precursorshexabromobenzene (C6Br6); sodium ethylthiolate (C2H5-SNa)
Solvents1,3-dimethyl-2-imidazolidinone (DMEU)
Additivessodium particles; hydrochloric acid workup
Atmospherenitrogen
Temperature100
Time56
Oxidant / reductantsodium particles used to stabilise benzenehexathiolate anions
Work-uppoured into hydrochloric acid; precipitate filtered and washed with water and acetone
Show 5 structured reagent records
RoleReagentAmount / concentrationSource
LinkerC6Br614 mmol in general method15755 · Results and Discussion - Synthesis of BHT · Table 1
AdditiveC2H5-SNa0.21 mol in general method15755 · Results and Discussion - Synthesis of BHT · Table 1
SolventDMEU30 mL15755 · Results and Discussion - Synthesis of BHT · Table 1
Reductantsodium particles0.644 g, 28 mmol15755 · Results and Discussion - Synthesis of BHT · Table 1
Acidhydrochloric acid150 mL · 1.0 M15755 · Results and Discussion - Synthesis of BHT · Table 1
Partial recipeSource: Main

Route 10: Other

15755 · Results and Discussion - Synthesis of BHT · Table 1

Metal precursorsnone
Linker precursorshexabromobenzene (C6Br6); sodium isopropylthiolate (i-C3H7-SNa)
Solvents1,3-dimethyl-2-imidazolidinone (DMEU)
Additivessodium particles; hydrochloric acid workup
Atmospherenitrogen
Temperature100
Time30
Oxidant / reductantsodium particles used to stabilise benzenehexathiolate anions
Work-uppoured into hydrochloric acid; precipitate filtered and washed with water and acetone
Show 5 structured reagent records
RoleReagentAmount / concentrationSource
LinkerC6Br614 mmol in general method15755 · Results and Discussion - Synthesis of BHT · Table 1
Additivei-C3H7-SNa0.21 mol in general method15755 · Results and Discussion - Synthesis of BHT · Table 1
SolventDMEU30 mL15755 · Results and Discussion - Synthesis of BHT · Table 1
Reductantsodium particles0.644 g, 28 mmol15755 · Results and Discussion - Synthesis of BHT · Table 1
Acidhydrochloric acid150 mL · 1.0 M15755 · Results and Discussion - Synthesis of BHT · Table 1