New fluorene‐based copolymers containing oxadiazole pendant groups: Synthesis, characterization, and polymer stability

Bondarev, Dmitrij; Zednı́k, Jiřı́; Vohlı́dal, Jiřı́; Podhájecká, Klára; Sedláček, Jan

doi:10.1002/pola.23506

Cited by 16 publications

(7 citation statements)

References 69 publications

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“…Polythiophenes exhibit one of the highest differences between the solution and solid state absorption maxima, up to 100 nm. For example in polyfluorene (co) polymers these differences hardly exceed 5 nm [25,26]. The large differences between solution and solid state absorption and emission testifies for the strong solid-state-induced interactions between polymer main chains which result in effective packing, strong p-p interactions and induced conformational ordering.…”

Section: Introductionmentioning

confidence: 98%

Polythiophene-based conjugated polyelectrolyte: Optical properties and association behavior in solution

et al. 2015

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Section: Introductionmentioning

confidence: 98%

Polythiophene-based conjugated polyelectrolyte: Optical properties and association behavior in solution

et al. 2015

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“…However, the polymer based fluorene is easy to generate aggregation in solid state, which may influence the color purity degree and the stability of the emitting light color. 27 The UV result shows that the incorporation of pentafluorobenzene in PFFTPD can avoid aggregation in some extent, which is expected to improve the polymer color purity and stability of emitting light colors.…”

Section: Scheme I Synthetic Routes Of Monomers and Copolymersmentioning

confidence: 98%

Enhanced thermo-stability and luminecent property of D-A copolymer based on fluorene and thieno[3,4-c]pyrrole-4,6-dione by incorporation of pentafluorobenzene group

et al. 2014

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A new monomer 1,3-dibromo-5-perfluorophenyl-thieno [3,4-c]pyrrole-4,6-dione was synthesized and the corresponded D-A copolymer poly{9, 9-dioctylfluorene-2,7-diyl-alt-5-perfluorophenylthieno[3,4-c]pyrrole-4,6-dione} (PFFTPD) based on fluorene unit was synthesized. In order to investigate the effect of pentafluorobenzene substitution on the photo-physics and stability properties, the compared D-A copolymer poly{9,9-dioctylfluorene-2,7-diylalt-5-octylthieno [3,4-c]pyrrole-4,6-dione} (PFCTPD) based on fluorene and octyl-thieno[3,4-c]pyrrole-4,6-dione was synthesized also. The obtained copolymer PFFTPD had a weight average molecular weight of 12178 with a narrow polydispersity index of 1.51, good solubility and higher thermal stability with T g of 131 o C and T d of 410 o C. Compared to that of PFCTPD, the PL spectra of PFFTPD in solution and in thin film showed narrower half peak width and weaker shoulder peak in the long wavelength region. The luminescent efficiency and color purity were enhanced while lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) levels were decreased by incorporation of pentafluorobenzene group. Thus, the copolymer PFFTPD may be good candidate as emitting material applied in polymer light emitting diode (PLED).

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“…The π‐conjugated polymers (CP), e.g., polyacetylenes, poly(arylene)s, poly( para ‐phenylenevinylene)s, and poly( para ‐phenyleneethynylene)s have become an important class of materials with a wide variety of applications, including light‐emitting diodes (LEDs), light‐emitting electrochemical cells (LECs), plastic lasers, solar cells, field‐effect transistors (FETs) and porous materials …”

Section: Introductionmentioning

confidence: 99%

“…materials with a wide variety of applications, [1][2][3][4][5][6][7][8] including light-emitting diodes (LEDs), [ 9 ] light-emitting electrochemical cells (LECs), [ 10 ] plastic lasers, [ 11 ] solar cells, [ 12 ] fi eld-effect transistors (FETs) [ 13 ] and porous materials. [ 14,15 ] The π-conjugated polyelectrolytes (CPEs) represent a special subclass of CPs.…”

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confidence: 99%

Ionic π‐Conjugated Polyelectrolytes by Catalyst Free Polymerization of Bis(pyridyl)acetylenes and Bis[(pyridyl)ethynyl]benzenes

Faukner

Trhlíková

Zednı́k

et al. 2015

Macro Chemistry & Physics

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The spontaneous, catalyst free polymerization of four monomers of the bis(pyridyl)acetylene and bis[(pyridyl)ethynyl]benzene types containing either 2-pyridyl or 4-pyridyl groups via activation with benzyl bromide leads to ionic π-conjugated polyacetylene-type polyelectrolytes (CPEs). All polymers are characterized by means of NMR, IR, UV/vis and photoluminescence spectroscopies, thermogravimetric analysis (TGA) and matrix assisted laser desorption/ ionization time of fl ight mass spectrometry (MALDI-TOF MS). The position of the pyridyl groups in the monomer infl uences the degree of quaternization and the extent of conjugation of CPEs. Monomers with 4-pyridyl groups provide CPEs with a low extent of quaternization [N + /(N + + N) = 0.27-0.34] and high extent of conjugation. On the other hand, the CPEs derived from 2-pyridyl-containing monomers are highly quaternized [N + /(N + + N) = 0.77-1.00], however, possess lower conjugation of the main chains. The mechanism assuming quaternization and polymerization as competitive reactions is proposed to explain the difference in the extent of quaternization of CPEs. Prepared CPEs i) are well soluble in polar solvents, e.g., water, methanol, dimethyl sulfoxide, and dimethylformamide, ii) exhibit photoluminescence (emission in the violet to yellow region), and iii) possess high thermal stability. materials with a wide variety of applications, [1][2][3][4][5][6][7][8] including light-emitting diodes (LEDs), [ 9 ] light-emitting electrochemical cells (LECs), [ 10 ] plastic lasers, [ 11 ] solar cells, [ 12 ] fi eld-effect transistors (FETs) [ 13 ] and porous materials. [ 14,15 ] The π-conjugated polyelectrolytes (CPEs) represent a special subclass of CPs. [ 16 ] The CPE polymers comprise π-conjugated main chains and ionic and/or ionizable groups. Unlike the majority of neutral CPs, CPEs additionally exhibit i) solubility in polar solvents as water, aqueous solutions, alcohols, and others environmentally friendly solvents, [17][18][19] ii) amphiphilic nature, which gives CPE macromolecules capability of self-assembling in solutions and ability to interact specifi cally with particular species under measurable optical and/or electrical responses, and iii) simultaneous electronic and ionic conductivity [ 20 ] reducing the electron-injection barrier Emission spectra 400 450 500 550 600 650 Wavelength (nm) Br N N N N N N N N N N Br Br Br Br Br NO CATALYST poly(4PD)

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New fluorene‐based copolymers containing oxadiazole pendant groups: Synthesis, characterization, and polymer stability

Cited by 16 publications

References 69 publications

Polythiophene-based conjugated polyelectrolyte: Optical properties and association behavior in solution

Polythiophene-based conjugated polyelectrolyte: Optical properties and association behavior in solution

Enhanced thermo-stability and luminecent property of D-A copolymer based on fluorene and thieno[3,4-c]pyrrole-4,6-dione by incorporation of pentafluorobenzene group

Ionic π‐Conjugated Polyelectrolytes by Catalyst Free Polymerization of Bis(pyridyl)acetylenes and Bis[(pyridyl)ethynyl]benzenes

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