Chapter 4. Novel chemosensory materials based on Side-Chain Polymer Containing
4.5 Conclusions
In conclusion, a novel side chain conjugated polymer containing pyridyl group in the Pendant was synthesized and its ability to sense metal ions was monitored by the
absorption and fluorescence emission spectra. The polymer can coordinate with many transition metals and the fluorescence was quenched or shifted by the addition of metal ions. The introduction of pyridyl groups into the conjugated polymer enhanced the efficiency of the energy or electron transfer reaction from the conjugated segments to the metal complex. Furthermore, the fluorescence of P1 can be recovered upon the addition of PMDTA to the P1-Cu2+ complexes solution, which is important for the practical use of chemosensor.
Chapter 5
Conclusions
In conclusions, first, a series of novel H-bonded acceptor copolymers containing different molar ratios of hole-transporting carbazole (CAZ) units and light-emitting PBB moieties (bearing three conjugated aromatic rings and a terminal H-acceptor),
were successfully synthesized. By the complementary surroundings via the complexation with different generations of OXD dendritic donors (G1COOH−G3COOH), the emission wavelengths of H-acceptor copolymers can be easily adjusted in their self-assembled structures of H-bonded side-chain dendritic complexes. As a result, all light-emitting, hole-transporting, and charge-transporting groups possessing novel photophysical and thermal properties are obtained in the supramolecular side-chain copolymers (i.e., H-bonded side-chain dendritic complexes). Moreover, the incorporation of carbazole units in the acceptor copolymers shows higher glass transition temperatures than the acceptor homopolymer itself and the emission wavelengths of H-acceptor polymers can be tuned (up to 61 nm of red-shift) by H-bonds. In addition, the larger dendritic size (i.e., the higher generation) of H-donors can afford stronger site-isolation and dendron-dilution effects, and thus better energy-transfer phenomena can be achieved.
The PLED devices with the configuration of ITO/PEDOT:PSS/(P4 or its H-bonded
dendritic complexes)/BCP/Alq3/LiF/Al were fabricated, and the emission colors from blue to green can be effectively tuned by incorporating various generations of OXD dendritic donors in the supramolecular side-chain polymer structures.
Second, a series of well-defined H-bonded side chain mesogenic copolymer networks containing proton acceptor emitter PBB with different molar ratios of proton donor benzoic acid (BA) were successfully synthesized. The polymers P1−P5 and full H-bonded polymers networks P1/P5 show enantiotropic mesomorphic behavior and give rise to mesomorphic glasses at room temperature. Compared with acceptor homopolymer P1, the H-bonded copolymer networks P2−P4 exhibit red-shifted PL emissions that due to H-boned effect. In addition, the higher benzoic acid contents in H-bonded copolymer networks have higher dilution effect than lower benzoic acid contents one, thereby the higher benzoic acid contents can be efficiently minimize interchain interaction and lower the aggregation extent between emitter PBB cores.
So the benzoic acids play both roles as solid solvents and H-bonded donors at the same time in H-bonded copolymer networks system. The four-layer PLED devices with the configuration of ITO/PEDOT:PSS/(P1 or its H-bonded networks)/BCP/Alq3/LiF/Al were fabricated, and effectively tuned the emission color from greenish-blue to green by the incorporation BA moieties donors in the H-bonded networks containing acceptor emitter PBB through a H-bonded self-assembly process.
In addition, a multilayered PLED device containing fully H-bonded cross-linking copolymer P2 showed EL emission of 537 nm under a turn-on voltage of 8.5 V, with a maximum luminance of 268 cd/m2 at 22 V and a luminance efficiency of 0.152 cd/A at 100 mA/cm2.
Finally, a novel side chain conjugated polymer containing pyridyl group in the Pendant was synthesized and its ability to sense metal ions was monitored by the absorption and fluorescence emission spectra. The polymer can coordinate with many transition metals and the fluorescence was quenched or shifted by the addition of metal ions. The introduction of pyridyl groups into the conjugated polymer enhanced the efficiency of the energy or electron transfer reaction from the conjugated segments to the metal complex. Furthermore, the fluorescence of P1 can be recovered upon the addition of PMDTA to the P1-Cu2+ complexes solution, which is important for the practical use of chemosensor.
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Appendix
Powder X-ray diffraction (XRD) Installation. Synchrotron powder X-ray
diffraction (XRD) measurements were performed in transmission mode with synchrotron radiation at beamline BL17A of the National Synchrotron Radiation Research Center (NSRRC), Taiwan, where the X-ray wavelength was 1.334431 Å.
The XRD data were collected using imaging plates (IP, of an area = 20 × 40 cm2 and a pixel resolution of 100) curved with a radius equivalent to the sample-to-image plate distance of 280 mm, and the diffraction signals were accumulated for 10 min. The powder samples were packed into a capillary tube and heated by a heat gun, where the temperature controller is programmable by a PC with a PID feed back system. The scattering angle theta was calibrated by a mixture of silver behenate and silicon. Note:
In the XRD experiments, the background scattering data were subtracted from the sample scans.
Figure A1 1H-NMR spectra of monomers PBB (M1) and CAZ (M2), and
Figure A2 Polarized optical micrograph (POM) image of homopolymer P1 exhibited a weak birefringent region in the nematic phase at 90 °C (heating).
2 4 6 8 10 12 14 16 18 20 22 24 26
Intensity (a.u.)
2θ (degree)
Figure A3 Powder X-ray diffraction (XRD) intensity against angle profiles obtained in the nematic phase of homopolymer P1 at 90 °C (heating).
300 350 400 450 500 550 600 650 0.0
0.2 0.4 0.6 0.8 1.0
Absorbance (a.u.)
Wavelength (nm)
P1 (HPBB) P2 (PBB-CAZ1) P3 (PBB-CAZ5) P4 (PBB-CAZ9)
Figure A4 Absorption spectra of polymers P1−P4 are normalized at the maximum absorption of light-emitting PBB segments in solid films.
O
300 350 400 450 500 550
0.0
Figure A5 (a) Chemical structure of model compound 1 and (b) the spectral overlap in the emission of model compound 1 and homopolymer P5 and the absorption of homopolymer P1 in THF solutions. Note: excited at 305 nm for model compound 1 and homopolymer P5.
Figure A6 1H-NMR spectra of monomers PBB (M1) and BA (M2), and BAMe (M3) in DMSO-d6.
Figure A7 1H-NMR spectra of polymers P1–P6 in DMSO-d6.
學經歷資料
1. Po-Jen Yang and Hong-Cheu Lin*, “Synthesis and characterization of achiral banana-shaped liquid crystalline molecules containing bisnaphthyl moieties”, Liquid Crystals, 2006, 33, 587-603.
2. Po-Jen Yang, Chung-Wen Wu, Duryodhan Sahu, and Hong-Cheu Lin* “Study of Supramolecular Side-Chain Copolymers ContainingLight-Emitting H-Acceptors and Electron-Transporting Dendritic H-Donors”, Macromolecules, 2009, 41, 9692.
3. Po-Jen Yang, Ling-Yung Wang, Chieh-Yin Tang, and Hong-Cheu Lin*, “Polymeric Dopant Effects of Bent-Core Covalent- and Hydrogen-Bonded Structures on Banana-Shaped Liquid Crystalline Complexes” Journal of Polymer Science: Part A:
Polymer Chemistry, 2009, Accepted.
List of Publications
1. Po-Jen Yang and Hong-Cheu Lin*, “Synthesis and characterization of achiral banana-shaped liquid crystalline molecules containing bisnaphthyl moieties”, Liquid Crystals, 2006, 33, 587-603.
2. Po-Jen Yang, Chung-Wen Wu, Duryodhan Sahu, and Hong-Cheu Lin* “Study of Supramolecular Side-Chain Copolymers ContainingLight-Emitting H-Acceptors and Electron-Transporting Dendritic H-Donors”, Macromolecules, 2009, 41, 9692.
3. Po-Jen Yang, Ling-Yung Wang, Chieh-Yin Tang, and Hong-Cheu Lin*, “Polymeric Dopant Effects of Bent-Core Covalent- and Hydrogen-Bonded Structures on Banana-Shaped Liquid Crystalline Complexes” Journal of Polymer Science: Part A:
Polymer Chemistry, 2009, Accepted.