3,4-Dithia-7H-cyclopenta[a]pentalene Chemical Properties

Melting point:

71.0 to 75.0 °C

Boiling point:

307.8±22.0 °C(Predicted)

Density 

1.400

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

soluble in Toluene

form 

powder to crystal

color 

White to Light yellow to Dark green

λmax

305nm(EtOH)(lit.)

InChI

InChI=1S/C9H6S2/c1-3-10-8-6(1)5-7-2-4-11-9(7)8/h1-4H,5H2

InChIKey

UITASDKJJNYORO-UHFFFAOYSA-N

SMILES

C12C3SC=CC=3CC=1C=CS2

CAS DataBase Reference

389-58-2

Safety Information

HS Code 

2934.99.4400

3,4-Dithia-7H-cyclopenta[a]pentalene Usage And Synthesis

Description

4H-cyclopenta[2,1-b:3,4-b′]dithiophene, also known as CPDT, a rigid coplanar structure favouring π?π intermolecular interactions with good electron-donating properties, has been one of the most attractive building blocks for organic field effect transistors and organic electronics. The five-member ring in the middle also offer the function to have side-chain manipulation to enhance solubility in solutions for device fabrications, morphology and polymer processing. One of the intensively studied polymer for organic electrons, PCPDTBT, with the alternating CPDT and 2,1,3- benzothiadiazole (BT) units, has demonstrated device performance of PCE over 6% [5]

Uses

4H-Cyclopenta[2,1-b:3,4-b'']dithiophene is useful in the synthesis of donor-acceptor copolymers.

Synthesis

General procedure for the synthesis of cyclopentylbithiophene from 4H-cyclopenta[2,1-B:3,4-B']dithiophen-4-one: Compound 77 (96 mg, 0.499 mmol), hydrazine monohydrate (268 mg, 5.35 mmol), potassium hydroxide (294 mg, 5.249 mmol), and ethylene glycol (5 mL) were added to a pre-dried and corked test tube in a pre-dried and corked test tube. The mixture was slowly heated from room temperature to 190 °C and refluxed at this temperature for 13 hours. Upon completion of the reaction, the mixture was cooled to room temperature, water was added and the organic phase was extracted with ether. The organic phase was washed sequentially with water and brine, dried with anhydrous magnesium sulfate and subsequently concentrated under reduced pressure. Purification by silica gel column chromatography (eluent: hexane/ethyl acetate = 10:1, v/v) afforded cyclopentylthiophene K (59 mg, 66% yield) as a white solid. Compound K was characterized as follows: oxidation potential of 0.68 V and reduction potential of -2.88 V measured by cyclic voltammetry (CV); maximum absorption wavelength of 310 nm in the UV-visible absorption spectrum; thin-layer chromatography (TLC) Rf=0.7 (unfolding agent: hexane/ dichloromethane=2:1, v/v); 1H NMR (270 MHz, CDCl3) δ: 7.17 (d, 2H, J=4.8 Hz), 7.09 (d, 2H, J=4.8 Hz), 3.54 (s, 2H); gas chromatography-mass spectrometry (GC-MS, EI) m/z: 178 (M+).

References

[1] Synlett, 2014, vol. 25, # 10, p. 1466 - 1472
[2] Inorganic Chemistry, 2016, vol. 55, # 13, p. 6653 - 6659
[3] Patent: EP1997821, 2008, A1. Location in patent: Page/Page column 32
[4] Macromolecules, 2003, vol. 36, # 8, p. 2705 - 2711
[5] Macromolecules, 2010, vol. 43, # 2, p. 697 - 708

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