Synthesis · Truxone-Based Conductive Metal-Organic Frameworks for the Oxygen Reductive Reaction

6 structured synthesis routes

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

Complete recipeSource: Both

Route 1: Other

p002 / article p.12691 · Experimental Section · Scheme S1

Linker precursors5,6-dihydroxy-1-indanone (2)

SolventsDMF

AdditivesK2CO3 base; bromobutane alkylating reagent

Temperature50

Time12

Work-upSolvent removed by rotary evaporation; extraction to remove excess base; column chromatography on silica with dichloromethane/petroleum ether.

Scalability context100 mL flask, gram-scale precursor.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	5,6-dihydroxy-1-indanone (2)	1.00 g, 6.1 mmol	p002 / article p.12691 · Experimental Section · Scheme S1
Other	bromobutane	2.51 g, 18.3 mmol	p002 / article p.12691 · Experimental Section · Scheme S1
Base	K2CO3	3.37 g, 24.4 mmol	p002 / article p.12691 · Experimental Section · Scheme S1
Solvent	DMF	40 mL	p002 / article p.12691 · Experimental Section · Scheme S1

Complete recipeSource: Both

Route 2: Other

p002 / article p.12691 · Experimental Section · Scheme S1

Linker precursors5,6-dimethoxy-1-indanone (1)

Solventsdry CH2Cl2

Temperature-40 then room temperature

Time3 h at -40 deg C plus 30 min after water quench

Oxidant / reductantboron tribromide

Work-upWater quench; vacuum filtration; washed with EtOH, water and CH2Cl2 until supernatant transparent.

ActivationDried under reduced pressure.

Scalability context250 mL flask, gram-scale precursor.

Show 3 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	5,6-dimethoxy-1-indanone (1)	2.44 g, 12.7 mmol	p002 / article p.12691 · Experimental Section · Scheme S1
Solvent	dry CH2Cl2	60 mL plus 20 mL for BBr3 solution	p002 / article p.12691 · Experimental Section · Scheme S1
Oxidant	boron tribromide	6.26 g, 25.4 mmol	p002 / article p.12691 · Experimental Section · Scheme S1

Complete recipeSource: Both

Route 3: Other

p002 / article p.12691 · Experimental Section · Scheme S1

Linker precursors5,6-dibutoxy-1-indanone (3)

Solventstoluene

Additivesethylene glycol; p-toluene sulfonic acid

Temperaturereflux

Time24

Work-upToluene removed under vacuum; crude product purified by silica-gel chromatography with 4:1 dichloromethane:petroleum ether.

Scalability context100 mL flask, gram-scale precursor.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	5,6-dibutoxy-1-indanone (3)	1.00 g, 3.6 mmol	p002 / article p.12691 · Experimental Section · Scheme S1
Additive	ethylene glycol	33.6 uL, 0.6 mmol	p002 / article p.12691 · Experimental Section · Scheme S1
Acid	p-toluene sulfonic acid	2.29 g, 1.2 mmol	p002 / article p.12691 · Experimental Section · Scheme S1
Solvent	toluene	40 mL	p002 / article p.12691 · Experimental Section · Scheme S1

Complete recipeSource: Both

Route 4: Other

p002 / article p.12691 · Experimental Section · Scheme S1

Linker precursors2,3,7,8,12,13-hexabutoxyl truxene (4)

Solventstetrahydrofuran; dichloromethane; petroleum ether

Additivespotassium tert-butoxide; NaHCO3 quench

Atmosphereair; flask open

Temperatureroom temperature

Time1

Oxidant / reductantair/O2 exposure during open-flask reaction

Work-upQuenched by NaHCO3 solution; extracted with dichloromethane; column chromatography with dichloromethane and petroleum ether.

Scalability context50 mL flask, 0.50 g precursor.

Show 3 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	2,3,7,8,12,13-hexabutoxyl truxene (4)	0.50 g, 0.65 mmol	p002 / article p.12691 · Experimental Section · Scheme S1
Base	potassium tert-butoxide	0.22 g, 1.9 mmol	p002 / article p.12691 · Experimental Section · Scheme S1
Solvent	tetrahydrofuran	25 mL	p002 / article p.12691 · Experimental Section · Scheme S1

Complete recipeSource: Both

Route 5: Other

p002 / article p.12691 · Experimental Section · Scheme S1; Figures S5-S7

Linker precursors2,3,7,8,12,13-hexabutoxyl truxone (5)

Solventsdichloromethane; water quench

Temperatureroom temperature

Time24

Oxidant / reductantboron tribromide

Work-upWater quench; product obtained by filtration.

Scalability context0.20 g protected truxone precursor.

Show 3 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	2,3,7,8,12,13-hexabutoxyl truxone (5)	0.2 g, 0.24 mmol	p002 / article p.12691 · Experimental Section · Scheme S1; Figures S5-S7
Solvent	dichloromethane	20 mL	p002 / article p.12691 · Experimental Section · Scheme S1; Figures S5-S7
Oxidant	boron tribromide in dichloromethane	1.03 mL · 1 mol L-1	p002 / article p.12691 · Experimental Section · Scheme S1; Figures S5-S7

Complete recipeSource: Both

Route 6: Liquid Liquid Interface

S10 · Synthesis of the truxone-Cu based MOF · Scheme S2; Figure S8

Metal precursorsCu(OAc)2

Linker precursors2,3,7,8,12,13-hexahydroxyl truxone

Solventsethyl acetate; water; acetone wash

Atmospherenot specified; beaker wrapped in plastic

Temperature30

Time48

Work-upReddish black powder collected through vacuum filtration and washed with 20 mL water, 20 mL ethyl acetate and 20 mL acetone.

ActivationVacuum drying at 85 deg C for 24 h to remove absorbed acetone.

Scalability context1000 mL beaker, 48 mg linker, 200 mL ethyl acetate and 200 mL water phases.

Show 5 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	2,3,7,8,12,13-hexahydroxyl truxone	48.0 mg, 1 eq.	S10 · Synthesis of the truxone-Cu based MOF · Scheme S2; Figure S8
Solvent	ethyl acetate (EA)	200 mL	S10 · Synthesis of the truxone-Cu based MOF · Scheme S2; Figure S8
Metal Source	Cu(OAc)2	27.2 mg, 1.5 equivalents	S10 · Synthesis of the truxone-Cu based MOF · Scheme S2; Figure S8
Solvent	water	200 mL	S10 · Synthesis of the truxone-Cu based MOF · Scheme S2; Figure S8
Solvent	acetone	20 mL wash	S10 · Synthesis of the truxone-Cu based MOF · Scheme S2; Figure S8