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Research on Synthesis and Luminescent Properties of Polythiophenes with Dioxane Group

Author: LiRong
Tutor: ZhongGuoLun
School: Zhejiang University
Course: Polymer Chemistry and Physics
Keywords: Polythiophene derivatives 1,3 - dioxane Synthesis Characterization Optical performance Cyclic voltammetry
CLC: O631.3
Type: Master's thesis
Year: 2010
Downloads: 61
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Abstract


Polythiophene and its derivatives having a high conductivity, good oxidation reduction reversibility concern fast transform with the change of the voltage characteristics of the emission color, and good environmental stability, etc., and in the nonlinear optical device, the polymeric luminescent diodes, gas sensors, organic transistors, as well as electric photochromic devices, etc. has a good prospect. Recently, many studies are still committed to the the polythiophene polymer synthesis, and great progress has been made in order to find and has good stability, processing, and light-emitting properties of novel polythiophene material. Side chain contains a 1,3 - dioxane ring substituents were synthesized two novel polythiophene derivatives, poly 3 - (1,3 - dioxan-2 - ethyl) thiophene (PDT), and poly-3 - (1,3 - ah-2 - ethyl) -4 - methyl-thiophene (PDMT), the specific process is as follows: First to the 3 - bromo-thiophene and 3 - bromo-4 - methyl-thiophene as raw material, no water the FeCl3 oxidation catalyst France were synthesized poly 3 - bromothiophene (PBRT), poly-3 - bromo-4 - methyl-thiophene (PBrMT), two kinds of random homopolymer; then each PBrT, PBrMT the reactants, Ni (dppp) Cl2 as a catalyst, were synthesized by the Grignard reaction PDT and PDMT found that these polymers are soluble in chloroform, dichloromethane, tetrahydrofuran, etc., a variety of common organic solvents. NMR analysis (NMR), infrared analysis (IR), and gel permeation chromatography (GPC), thermal gravimetric analysis (TGA) and other means of its chemical structure, molecular weight, thermal stability were carried out to characterize and test. NMR analysis showed that more than about 80% of the bromine atom in the 3 - (1,3 - ah alkoxy -2 - ethyl) synthesized in PDT and PDMT substituted; they have a high molecular weight and narrow molecular weight distribution ; good thermal stability, high temperature environment can be used to a certain extent. A comparative study of these polymers UV - visible absorption properties and photoluminescence properties. The results show that: (1) dilute chloroform solution of the polymer and the spin-coated films having different degrees of light emitting activity; (2) the substituted the yl high steric hindrance and two oxygen atoms electrically negative-acting, PDT and the emission peak in PDMT respectively than PBrT PBrMT peak has a certain degree of the blue shift, respectively emitting orange shade and green light; after the introduction of a methyl group in the (3) PDMT 4, its emission wavelength of more than PDT The large degree of blue shift. The PDT and PDMT of redox properties, and a combination of UV - visible spectrum calculated their energy level and the energy gap value was studied by cyclic voltammetry, specific conclusions are as follows: PDT and PDMT EHOMO to -5.34 eV, -5.98 eV , ELUMO is -3.15 eV and -3.61 eV energy gap E. Were 2.19 eV, 2.37 eV, the experimental results show that, PDT and PDMT of as the emitting material can be applied to the organic electroluminescent device. Respectively the PDT and PDMT the light absorption properties and light-emitting properties and has a similar structure of the poly 3 - ring hexyl-thiophene thiophene (PCHT) and poly 3 - cyclohexyl -4 - methyl-thiophene thiophene (PCHMT) (cited since literature) conducted a comparison, Found of PDT and PDMT of 3-substituted group in the cyclic structure containing two O atoms, and between two methylene connected dioxane thiophene electronegative oxygen atom and a substituent steric interaction effects, resulting the PDT solution absorption and emission wavelengths than the corresponding values ​​of the PCHT blue shift of a certain degree of the same, but the absorption wavelength of the film; PDMT solution absorption wavelength, emission wavelength of the wavelength and the absorption of the film are respectively compared PCHMT the corresponding values ​​of a certain degree of red-shift.

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CLC: > Mathematical sciences and chemical > Chemistry > Polymer chemistry ( polymer ) > Polymer physics and physical chemistry of polymers > The chemical nature of polymers
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