Furan → Pentacene

HRID 574017

Reaction equation

HRID 574017 reaction equation
O1[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:6]12[CH2:12][C:9](=[CH:10][CH:11]=1)[C:8]1C=CC=C[C:7]2=1>>[CH:2]1[C:3]2[C:4](=[CH:5][C:8]3[C:9]([CH:2]=2)=[CH:10][C:11]2[C:6](=[CH:12][C:11]4[C:6]([CH:12]=2)=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:7]=3)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8029FuranHCID 566125711,4-Methanonaphthalene

Product 1

HCID 8671PentaceneYield 40%

Conditions

Temperature
128 °C

Procedure

In summary, a new stable and soluble pentacene precursor 2 was synthesized in 40% yield from the cycloaddition of a furan derivative 3 and a benzonorbornadiene 4. Compound 2 releases a unit of CO upon heating at 128° C. or by irradiation with UV light (366 nm) to produce pentacene in nearly quantitative yield. Thin films of pentacene were prepared by spin-coating followed by thermal annealing, and found to display typical FET characteristics.

Workup

  1. customto produce pentacene in nearly quantitative yield

Sources & evidence

ORD record
ord-dcfaaa3517ca4c8ea9c377fa52f530e3
Source dataset
uspto-grants-2015_05
Patent number
US09034439B2

Linked notes

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