Electrochemical and optical properties of substituted phthalimide based monomers and electrochemical polymerization of 3,4-ethylenedioxythiophene-polyhedral oligomeric silsesquioxane (POSS) analogue

• Published in: Dyes and pigments Vol. 161; pp. 411 - 418
• Main Authors: Çakal, Deniz, Ertan, Salih, Cihaner, Atilla, Önal, Ahmet M.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01-02-2019
• Subjects: Donor-acceptor-donor approach; EDOT; Electrochromism; Electropolymerization; Phthalimide; POSS; Thiophene; Phthalimide; EDOT; Electrochromism; POSS; Thiophene; Donor-acceptor-donor approach; Electropolymerization
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2018.10.002

A new series of donor-acceptor-donor type trimeric monomers bearing substituted phthalimide units as acceptor units and thiophene and 3,4-ethylenedioxythiophene (EDOT) as donor units was synthesized and characterized. The strength of acceptor units and intramolecular charge transfer between donor and acceptor units were investigated by using electrochemical and optical methods. The main advantage of phthalimide unit over other acceptor units is the ease of its functionalizability. Thus, utilizing this property, a phthalimide derivative (E2P-POSS) bearing polyhedral oligomeric silsesquioxane (POSS) cage was introduced successfully with EDOT and polymerized electrochemically. The corresponding electroactive polymer, PE2P-POSS, has a band gap of 1.72 eV and is an electrochromic polymer: gray when neutralized and eggplant purple when oxidized.
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•Phthalimide units bearing different substituents were synthesized.•PR i-butyl POSS and PR substituted phthalimides were coupled with different donor units.•The strength of A units and ICT between D and A units were investigated by using CV and UV methods.•SPEL investigations showed that PE2P-POSS has relatively low Eg and is an electrochromic polymer.