Synthesis, properties and self-polymerization of 1,8-naphthalimide-based vinyl monomer

被引:0
作者
Gudeika, Dalius [1 ]
Peciulyte, Laura [1 ]
Grazulevicius, Juozas V. [1 ]
Obushak, Mykola D. [2 ]
机构
[1] Kaunas Univ Technol, LT Kaunas, Dept Polymer Chem & Technol, Kaunas, Lithuania
[2] Ivan Franko Natl Univ Lviv, Dept Organ Chem, Lvov, Ukraine
关键词
1; 8-Naphthalene imide; self-polymerization; activation energy; electron affinity; solid state ionization potential; DERIVATIVES; TRIPHENYLAMINE; CARBAZOLE; LINKAGES;
D O I
10.1080/15421406.2016.1255507
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
1,8-Naphthalene imide with reactive vinyl group was synthesized by Suzuki reaction. Self-polymerization of the compound starts at 177 degrees C as confirmed by differential scanning calorimetry. The electron affinity values of the monomer and the polymer were found to be -3.30eV and -3.05eV, respectively. The solid state ionization potential values of the monomer and the polymer were recorded to be 6.42eV and 6.17eV, respectively. The activation energy of the process was estimated using Ozawa method. It depends on the conversion degree and was found to be in the range of 136-195 kJ/mol. Pre-exponential factor values decrease during polymerization with decreasing chain mobility due to increasing molecular weight of the polymer.
引用
收藏
页码:30 / 38
页数:9
相关论文
共 21 条
[1]   Highly Soluble Monoamino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties [J].
Chen, Kew-Yu ;
Chang, Che-Wei .
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2014, 15 (12) :22642-22660
[2]   Pyrene-Based Materials for Organic Electronics [J].
Figueira-Duarte, Teresa M. ;
Muellen, Klaus .
CHEMICAL REVIEWS, 2011, 111 (11) :7260-7314
[3]   Influence of Alkyl Side-Chain Length on the Performance of Poly(3-alkylthiophene)/Polyfluorene All-Polymer Solar Cells [J].
Friedel, Bettina ;
McNeill, Christopher R. ;
Greenham, Neil C. .
CHEMISTRY OF MATERIALS, 2010, 22 (11) :3389-3398
[4]  
Frisch M.J., 2016, Gaussian, V16
[5]   Electron-transporting naphthalimide-substituted derivatives of fluorene [J].
Gudeika, D. ;
Reghu, R. R. ;
Grazulevicius, J. V. ;
Buika, G. ;
Simokaitiene, J. ;
Miasojedovas, A. ;
Jursenas, S. ;
Jankauskas, V. .
DYES AND PIGMENTS, 2013, 99 (03) :895-902
[6]   Synthesis and properties of the derivatives of triphenylamine and 1,8-naphthalimide with the olefinic linkages between chromophores [J].
Gudeika, Dalius ;
Sini, Gjergji ;
Jankauskas, Vygintas ;
Sych, Galyna ;
Grazulevicius, Juozas V. .
RSC ADVANCES, 2016, 6 (03) :2191-2201
[7]   Effect of Ethynyl Linkages on the Properties of the Derivatives of Triphenylamine and 1,8-Naphthalimide [J].
Gudeika, Dalius ;
Grazulevicius, Juozas V. ;
Volyniuk, Dmytro ;
Juska, Gytis ;
Jankauskas, Vygintas ;
Sini, Gjergji .
JOURNAL OF PHYSICAL CHEMISTRY C, 2015, 119 (51) :28335-28346
[8]   Structure-properties relationship of the derivatives of carbazole and 1,8-naphthalimide: Effects of the substitution and the linking topology [J].
Gudeika, Dalius ;
Grazulevicius, Juozas Vidas ;
Volyniuk, Dmytro ;
Butkute, Rita ;
Juska, Gytis ;
Miasojedovas, Arunas ;
Gruodis, Alytis ;
Jursenas, Saulius .
DYES AND PIGMENTS, 2015, 114 :239-252
[9]   Synthesis and characterization of thermally cross-linkable trimer based on triphenylamine [J].
Hong, Heeseob ;
Jo, Mi Young ;
Ha, Ye Eun ;
Kim, Joo Hyun .
MACROMOLECULAR RESEARCH, 2013, 21 (03) :321-326
[10]   Thermally cross-linkable hole transporting polymer synthesized by living anionic polymerization for effective electron blocking and reduction of exciton quenching in multilayer polymer light emitting diodes [J].
Kang, Beom-Goo ;
Kang, Hongkyu ;
Kang, Nam-Goo ;
Lee, Chang-Lyoul ;
Lee, Kwanghee ;
Lee, Jae-Suk .
POLYMER CHEMISTRY, 2013, 4 (04) :969-977