Abstract
A novel series of pyrene containing thiophene monomers TPM1–5 were synthesized and fully characterized by FTIR, MS, 1H- and 13C-NMR spectroscopy; their thermal properties were determined by TGA and DSC. These monomers were chemically polymerized using FeCl3 as oxidizing agent to give the corresponding oligomers TPO1–5) and they were electrochemically polymerized to obtain the corresponding polymer films deposited onto ITO. All oligomers exhibited good thermal stability, with T10 values between 255 and 299 °C, and Tg values varying from 36 to 39 °C. The monomers showed an absorption band at 345 nm due to the S0 → S2 transition of the pyrene group, whereas the fluorescence spectra showed a broad emission band arising from the “monomer” emission at 375–420 nm. The obtained polymers exhibited two absorption bands at 244 and 354 nm, due to the polythiophene and the pyrene moieties, respectively. The fluorescence spectra of polymers showed a broad “monomer” emission at 380–420 nm followed by an intense excimer emission band at 570 nm, due to the presence of intramolecular pyrene-pyrene interactions in these compounds.
Highlights
IntroductionThe synthesis and characterization of polymers containing heteroaromatic rings have been widely studied because of their potential in advanced optoelectronic applications [1,2,3,4,5]
In recent years, the synthesis and characterization of polymers containing heteroaromatic rings have been widely studied because of their potential in advanced optoelectronic applications [1,2,3,4,5].Polythiophene (PT) has been considered one of the most promising π-conjugated polymers due to its high stability, ease of structural modification and controllable optical and electrochemical properties.At the beginning the applications of non-substituted polythiophene were very limited because of its insolubility in many organic solvents, due to its extended π-conjugated structure
On the the other other hand, hand, the the emission emission spectra spectra of of the the polymers polymers (Figure 9) showed a well structured “monomer” emission band at ca. λ = 390–410 nm followed by a very intense broad excimer band at λ = 545 nm, which reveals the presence of intramolecular pyrene-pyrene interactions
Summary
The synthesis and characterization of polymers containing heteroaromatic rings have been widely studied because of their potential in advanced optoelectronic applications [1,2,3,4,5]. We carried out the incorporation of pyrene moieties into polythiophenes in order to obtain donor-acceptor systems for optical applications [29,30,31,38,39] These polymers can be synthesized either by chemical or electrochemical methods. The optical properties of the obtained polythiophenes were studied by absorption and fluorescence spectroscopies in solid state Due to their chromic properties, pyrene’s ability to form excimers and oxygen sensitivity, these oligomers and polymers can be used as sensors or as luminescent materials in OLEDs [41,42,43].
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