Synthesis · Synthesis and changes of conductivities and thermal stabilities of 4,4′-oxybis [N-(3,4-dihydroxybenzilidene) aniline] chelate polymers

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

2 · Section 2.2 · Scheme 2

Metal precursorsnone

Linker precursorsBis(4-aminophenyl)ether; 3,4-dihydroxybenzaldehyde

Solventsmethanol (60 mL + 20 mL)

Atmospherenot specified

Temperaturemethanol reflux/boiling

Time3

Work-upSchiff base precipitated, filtered, recrystallised from methanol, dried in a vacuum desiccator.

Activationvacuum desiccator drying

Scalability context250 mL three-necked round-bottom flask; yield 46%.

Show 3 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	Bis(4-aminophenyl)ether	0.2 g, 0.001 mol	2 · Section 2.2 · Scheme 2
Linker	3,4-dihydroxybenzaldehyde	0.414 g, 0.003 mol	2 · Section 2.2 · Scheme 2
Solvent	methanol	60 mL + 20 mL	2 · Section 2.2 · Scheme 2

Complete recipeSource: Main

Route 2: Other

2-3 · Section 2.3 · Scheme 3

Metal precursorsCd(AcO)2 · 2H2O

Linker precursors4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline] (3,4-HBA)

SolventsTHF (40 mL) plus methanol (10 mL metal-salt solution)

Atmospherenot specified

TemperatureTHF/methanol reflux/boiling

Time1

Work-upPolymer precipitated, filtered, washed with cold methanol/THF (1:1), dried in a vacuum oven.

Activationvacuum oven drying

Scalability context250 mL three-necked round-bottom flask; reported yield 11%.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline]	0.264 g, 6 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Metal Source	Cd(AcO)2 · 2H2O	0.213 g, 8 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Solvent	THF	40 mL	2-3 · Section 2.3 · Scheme 3
Solvent	methanol	10 mL	2-3 · Section 2.3 · Scheme 3

Complete recipeSource: Main

Route 3: Other

2-3 · Section 2.3 · Scheme 3

Metal precursorsCo(AcO)2 · 4H2O

Linker precursors4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline] (3,4-HBA)

SolventsTHF (40 mL) plus methanol (10 mL metal-salt solution)

Atmospherenot specified

TemperatureTHF/methanol reflux/boiling

Time1

Work-upPolymer precipitated, filtered, washed with cold methanol/THF (1:1), dried in a vacuum oven.

Activationvacuum oven drying

Scalability context250 mL three-necked round-bottom flask; reported yield 48%.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline]	0.264 g, 6 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Metal Source	Co(AcO)2 · 4H2O	0.200 g, 8 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Solvent	THF	40 mL	2-3 · Section 2.3 · Scheme 3
Solvent	methanol	10 mL	2-3 · Section 2.3 · Scheme 3

Complete recipeSource: Main

Route 4: Other

2-3 · Section 2.3 · Scheme 3

Metal precursorsCrCl3 · 6H2O

Linker precursors4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline] (3,4-HBA)

SolventsTHF (40 mL) plus methanol (10 mL metal-salt solution)

Atmospherenot specified

TemperatureTHF/methanol reflux/boiling

Time1

Work-upPolymer precipitated, filtered, washed with cold methanol/THF (1:1), dried in a vacuum oven.

Activationvacuum oven drying

Scalability context250 mL three-necked round-bottom flask; reported yield 92%.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline]	0.264 g, 6 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Metal Source	CrCl3 · 6H2O	0.213 g, 8 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Solvent	THF	40 mL	2-3 · Section 2.3 · Scheme 3
Solvent	methanol	10 mL	2-3 · Section 2.3 · Scheme 3

Complete recipeSource: Main

Route 5: Other

2-3 · Section 2.3 · Scheme 3

Metal precursorsCu(AcO)2 · H2O

Linker precursors4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline] (3,4-HBA)

SolventsTHF (40 mL) plus methanol (10 mL metal-salt solution)

Atmospherenot specified

TemperatureTHF/methanol reflux/boiling

Time1

Work-upPolymer precipitated, filtered, washed with cold methanol/THF (1:1), dried in a vacuum oven.

Activationvacuum oven drying

Scalability context250 mL three-necked round-bottom flask; reported yield 67%.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline]	0.264 g, 6 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Metal Source	Cu(AcO)2 · H2O	0.160 g, 8 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Solvent	THF	40 mL	2-3 · Section 2.3 · Scheme 3
Solvent	methanol	10 mL	2-3 · Section 2.3 · Scheme 3

Complete recipeSource: Main

Route 6: Other

2-3 · Section 2.3 · Scheme 3

Metal precursorsMnCl2

Linker precursors4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline] (3,4-HBA)

SolventsTHF (40 mL) plus methanol (10 mL metal-salt solution)

Atmospherenot specified

TemperatureTHF/methanol reflux/boiling

Time1

Work-upPolymer precipitated, filtered, washed with cold methanol/THF (1:1), dried in a vacuum oven.

Activationvacuum oven drying

Scalability context250 mL three-necked round-bottom flask; reported yield 24%.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline]	0.264 g, 6 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Metal Source	MnCl2	0.101 g, 8 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Solvent	THF	40 mL	2-3 · Section 2.3 · Scheme 3
Solvent	methanol	10 mL	2-3 · Section 2.3 · Scheme 3

Complete recipeSource: Main

Route 7: Other

2-3 · Section 2.3 · Scheme 3

Metal precursorsNi(AcO)2 · 4H2O

Linker precursors4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline] (3,4-HBA)

SolventsTHF (40 mL) plus methanol (10 mL metal-salt solution)

Atmospherenot specified

TemperatureTHF/methanol reflux/boiling

Time1

Work-upPolymer precipitated, filtered, washed with cold methanol/THF (1:1), dried in a vacuum oven.

Activationvacuum oven drying

Scalability context250 mL three-necked round-bottom flask; reported yield 45%.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline]	0.264 g, 6 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Metal Source	Ni(AcO)2 · 4H2O	0.199 g, 8 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Solvent	THF	40 mL	2-3 · Section 2.3 · Scheme 3
Solvent	methanol	10 mL	2-3 · Section 2.3 · Scheme 3

Complete recipeSource: Main

Route 8: Other

2-3 · Section 2.3 · Scheme 3

Metal precursorsPb(AcO)2 · 3H2O

Linker precursors4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline] (3,4-HBA)

SolventsTHF (40 mL) plus methanol (10 mL metal-salt solution)

Atmospherenot specified

TemperatureTHF/methanol reflux/boiling

Time1

Work-upPolymer precipitated, filtered, washed with cold methanol/THF (1:1), dried in a vacuum oven.

Activationvacuum oven drying

Scalability context250 mL three-necked round-bottom flask; reported yield 65%.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline]	0.264 g, 6 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Metal Source	Pb(AcO)2 · 3H2O	0.303 g, 8 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Solvent	THF	40 mL	2-3 · Section 2.3 · Scheme 3
Solvent	methanol	10 mL	2-3 · Section 2.3 · Scheme 3

Complete recipeSource: Main

Route 9: Other

2-3 · Section 2.3 · Scheme 3

Metal precursorsZn(AcO)2 · 2H2O

Linker precursors4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline] (3,4-HBA)

SolventsTHF (40 mL) plus methanol (10 mL metal-salt solution)

Atmospherenot specified

TemperatureTHF/methanol reflux/boiling

Time1

Work-upPolymer precipitated, filtered, washed with cold methanol/THF (1:1), dried in a vacuum oven.

Activationvacuum oven drying

Scalability context250 mL three-necked round-bottom flask; reported yield 55%.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline]	0.264 g, 6 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Metal Source	Zn(AcO)2 · 2H2O	0.176 g, 8 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Solvent	THF	40 mL	2-3 · Section 2.3 · Scheme 3
Solvent	methanol	10 mL	2-3 · Section 2.3 · Scheme 3

Complete recipeSource: Main

Route 10: Other

2-3 · Section 2.3 · Scheme 3

Metal precursorsZrCl4

Linker precursors4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline] (3,4-HBA)

SolventsTHF (40 mL) plus methanol (10 mL metal-salt solution)

Atmospherenot specified

TemperatureTHF/methanol reflux/boiling

Time1

Work-upPolymer precipitated, filtered, washed with cold methanol/THF (1:1), dried in a vacuum oven.

Activationvacuum oven drying

Scalability context250 mL three-necked round-bottom flask; reported yield 95%.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	4,4'-oxybis[N-(3,4-dihydroxybenzilidene)aniline]	0.264 g, 6 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Metal Source	ZrCl4	0.186 g, 8 x 10^-4 mol	2-3 · Section 2.3 · Scheme 3
Solvent	THF	40 mL	2-3 · Section 2.3 · Scheme 3
Solvent	methanol	10 mL	2-3 · Section 2.3 · Scheme 3