cMOF Evidence Base

Synthesis evidence

Interplay of structural dynamics and electronic effects in an engineered assembly of pentacene in a metal-organic framework

Haldar R., Kozlowska M., Ganschow M. et al. · Chemical Science · 2021 · 4477-4483

2 structured synthesis routes

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

Complete recipeSource: SI

Route 1: Other

2-5 · Synthesis of Pentacene linker · Fig. S1

Linker precursorspentacenequinone I; tetrachloropentacene II; dichloropentacene III; boronic acid IV; ester V
SolventsPOCl3; DMF; dioxane/H2O; THF/H2O
AdditivesPCl5; NaI; XPhos; Pd2dba3; K3PO4; KOH; HCl
Atmosphereflame-dried glassware; degassed solvent mixture for Suzuki step and hydrolysis
Temperature130; reflux; 100; 100
Time3; 0.5; 72; 24
Oxidant / reductantNaI; Pd-catalysed Suzuki coupling; KOH hydrolysis; HCl acidification
Work-upfiltration and washing after each step; final product filtered, washed with water, and dried under reduced pressure
Show 13 structured reagent records
RoleReagentAmount / concentrationSource
Otherpentacenequinone I3.00 g, 9.73 mmol2-5 · Synthesis of Pentacene linker · Fig. S1
Additivephosphorouspentachloride20.3 g, 97.3 mmol, 10.0 eq.2-5 · Synthesis of Pentacene linker · Fig. S1
Solventphosphorylchloride60 mL, 98.4 g, 662 mmol, 68.0 eq.2-5 · Synthesis of Pentacene linker · Fig. S1
Reductantsodiumiodide610 mg, 4.09 mmol, 0.45 eq.2-5 · Synthesis of Pentacene linker · Fig. S1
SolventDMF50 mL2-5 · Synthesis of Pentacene linker · Fig. S1
Linkerdichloropentacene III50.0 mg, 144 micromol2-5 · Synthesis of Pentacene linker · Fig. S1
Linkerboronic acid IV130 mg, 720 micromol, 5.00 eq.2-5 · Synthesis of Pentacene linker · Fig. S1
AdditiveXPhos20.6 mg, 43.2 micromol, 0.30 eq.2-5 · Synthesis of Pentacene linker · Fig. S1
AdditivePd2dba313.2 mg, 14.4 micromol, 0.10 eq.2-5 · Synthesis of Pentacene linker · Fig. S1
BaseK3PO4(aq)part of 5 mL 4:1 dioxane/K3PO4(aq) · 1.2 M2-5 · Synthesis of Pentacene linker · Fig. S1
Linkerpentacenederivative V250 mg, 457 micromol2-5 · Synthesis of Pentacene linker · Fig. S1
BaseKOH(aq)part of 30 mL THF/KOH(aq) · 15 M2-5 · Synthesis of Pentacene linker · Fig. S1
Acidconcentrated hydrochloric acid37%2-5 · Synthesis of Pentacene linker · Fig. S1
Partial recipeSource: Both

Route 2: Other

10 · Synthesis of Zn-Pn

Metal precursorszinc acetate
Linker precursorspentacene linker 1
Solventsethanol
AtmosphereO2 plasma substrate pretreatment; deposition atmosphere not specified
Substrate orientationsilicon substrates with [100] orientation; quartz glass
Work-upethanol rinse after metal or linker coating to remove unreacted species/by-products
ActivationO2 plasma treatment of substrates for 15 min to generate hydroxyl groups; no post-synthesis activation reported
Scalability contextThickness controlled by number of deposition cycles, but exact cycle count was not stated.
Show 6 structured reagent records
RoleReagentAmount / concentrationSource
Metal Sourcezinc acetate1 mM in ethanol10 · Synthesis of Zn-Pn
Linkerpentacene linker20 micromol/L in ethanol10 · Synthesis of Zn-Pn
SolventethanolNot specified10 · Synthesis of Zn-Pn
Othersilicon substrate[100] orientation10 · Synthesis of Zn-Pn
Otherquartz substrateNot specified10 · Synthesis of Zn-Pn
Oxidantoxygen plasma15 min10 · Synthesis of Zn-Pn