Cucurbit[7]uril‐Threaded Poly(3, 4‐ethylenedioxythiophene): A Novel Processable Conjugated Polyrotaxane. Issue 21 (29th January 2019)

• Record Type: Journal Article
• Authors: Farcas, Aurica; Assaf, Khaleel I.; Resmerita, Ana‐Maria; Sacarescu, Liviu; Asandulesa, Mihai; Aubert, Pierre‐Henri; Nau, Werner M.
• Other Names: Sauvage Jean‐Pierre guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 21(2019)
• Page Start: 3442
• Page End: 3450
• Publication Date: 2019-01-29
• Subjects: Host‐guest chemistry -- PEDOT -- Conductive polymers -- Functional materials -- Polyrotaxanes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801724
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The effect of cucurbit[7]uril (CB7) complexation on the solubility, thermal, optical, electrochemical, morphological, and electrical properties of poly(3, 4‐ethylenedioxythiophene) (PEDOT) was investigated. For this purpose, PEDOT polypseudorotaxane (PEDOT· CB7‐PS) was synthesized by the chemical oxidation of the corresponding 3, 4‐ethylenedioxythiophene (EDOT) inclusion complex with CB7 (EDOT· CB7) in water by using FeCl3 as catalyst. PEDOT· CB7‐PS is converted into the polyrotaxane (PEDOT· CB7‐PR) by end capping of the PEDOT backbones with bulky pyrene groups. The binding affinity ( K a = 1.5 × 10 4 m –1 ) confirmed sizeable binding of EDOT to CB7. FT‐IR, 1 H NMR, ESI‐MS, and DFT calculations were used to characterize the synthesized compounds. PEDOT· CB7‐PR showed interesting electrochemical characteristics, which are consistent with the optical and surface‐morphological results. In particular, the material exhibited n ‐ and p ‐doping processes and semiconducting properties. SAXS and TEM analyses of PEDOT· CB7‐PR indicated a tendency to self‐assemble. Abstract : A poly(3, 4‐ethylenedioxythiophene) polypseudorotaxane (PEDOT· CB7‐PS) and polyrotaxane (PEDOT· CB7‐PR) were synthesized. The threading of CB7 into the PEDOT backbones leads to distinct improvements in their solubility and film formation ability. The bright‐blue materials showed interesting optical and surface morphological properties, which were consistent with their electrochemical data.