Synthesis · Electrical conductivity and electroluminescence of a new anthracene-based metal-organic framework with π-conjugated zigzag chains

Partial recipeSource: SI

Route 1: Other

p004 · Synthesis of Ligand

Linker precursorsEthyl 4-ethynylbenzoate; 9,10-dibromoanthracene

SolventsDMF; Et3N; CHCl3; THF/methanol/H2O (1:1:1)

AdditivesPd(Ph3)2Cl2; CuI; KOH; aqueous HCl

AtmosphereN2 for coupling step

Temperature80 for coupling; reflux for hydrolysis

Time48 for coupling; 24 for hydrolysis

Work-upReaction quenched with water, extracted with CHCl3, washed with brine, dried over MgSO4, recrystallised from CHCl3; hydrolysis mixture acidified with aq. HCl and precipitate filtered.

Scalability contextCoupling step starts from 2.0 g ethyl 4-ethynylbenzoate and 1.74 g 9,10-dibromoanthracene; hydrolysis starts from 0.708 g intermediate.

Show 9 structured reagent records

Role	Reagent	Amount / concentration	Source
Linker	ethyl 4-ethynylbenzoate	2.0 g, 11.49 mmol	p004 · Synthesis of Ligand
Linker	9,10-dibromoanthracene	1.74 g, 5.18 mmol	p004 · Synthesis of Ligand
Solvent	DMF	20 mL	p004 · Synthesis of Ligand
Additive	Pd(Ph3)2Cl2	90 mg, 0.13 mmol	p004 · Synthesis of Ligand
Additive	CuI	45 mg, 0.24 mmol	p004 · Synthesis of Ligand
Base	Et3N	20 mL	p004 · Synthesis of Ligand
Solvent	THF/methanol/H2O (1:1:1)	45 mL	p004 · Synthesis of Ligand
Base	KOH	1.74 g, 12.64 mmol	p004 · Synthesis of Ligand
Acid	aq. HCl	not specified	p004 · Synthesis of Ligand

Partial recipeSource: Both

Route 2: Solvothermal

p004 · Synthesis of NNU-27

Metal precursorsZn(NO3)2.6H2O (13 mg); NaNO3 (15 mg)

Linker precursorsH2L (20 mg), 4,4'-(anthracene-9,10-diylbis(ethyne-2,1-diyl))-dibenzoic acid

SolventsN,N-diethylformamide (DEF, 10 mL)

AdditivesNaNO3

AtmosphereCapped vial; gas atmosphere not specified

Temperature85

Time72

Work-upAfforded orange needle-like crystals; isolation/washing/drying not specified

ActivationNo activation reported for synthesis; later solvent-exchange activation caused loss of pristine structure

Scalability context20 mL capped vial, ligand-scale 20 mg; yield ca. 60% based on ligand.

Show 4 structured reagent records

Role	Reagent	Amount / concentration	Source
Metal Source	Zn(NO3)2.6H2O	13 mg	p004 · Synthesis of NNU-27
Additive	NaNO3	15 mg	p004 · Synthesis of NNU-27
Linker	H2L	20 mg	p004 · Synthesis of NNU-27
Solvent	N,N-diethylformamide (DEF)	10 ml	p004 · Synthesis of NNU-27

Electrical conductivity and electroluminescence of a new anthracene-based metal-organic framework with π-conjugated zigzag chains

2 structured synthesis routes