Research article Special Issues

The synthesis of conjugated polymers with different length side chains and the effect on their nanoparticles

  • Received: 30 June 2018 Accepted: 22 August 2018 Published: 27 August 2018
  • In recent years, conjugated polymers (CPs) and their nanoparticles (CPNs) were widely concerned and applied in many fields due to their outstanding advantages such as higher absorption coefficients, good photostability, low toxicity and good biocompatibility. However, most reports were focused on their applications, and rare attentions were given on the synthesis of CPs and the effect factors of CPNs’ morphology and properties. In this work, four CPs (P1, P2, P3, P4) with different length side chains were synthetized by Wittig–Horner reaction and further used to prepare CPNs by the nano-precipitation method. The CPs and CPNs were characterized and analyzed by Hydrogen Nuclear Magnetic Resonance (1H NMR), gel permeation chromatography (GPC), Fourier transform infrared spectroscopy (FTIR), dynamic light scattering (DLS) and transmission electron microscope (TEM). The absorbance and fluorescence emission spectra of CPs in tetrahydrofuran (THF) and CPNs solutions with different length side chains were investigated, and their quantum yields (Фs) were calculated by the reference method. The results showed that the synthetic CPs have narrow polydispersity index. Some interesting phenomenon appeared with the increased side chain length. The molecular weights will reduce except P3, and the absorbance and fluorescence emission spectra of CPs and CPNs are red-shifted. Фs are better and enlarged for CPs and CPNs, and better dispersion and uniform size were founded with longer side chains.

    Citation: Qiu-bo Wang, Chao Xu, Yi-bao Jiang, Xian Zhang, Jin-shui Yao, Cong-de Qiao, Qin-ze Liu, Yuan-hong Zhang. The synthesis of conjugated polymers with different length side chains and the effect on their nanoparticles[J]. AIMS Materials Science, 2018, 5(4): 770-780. doi: 10.3934/matersci.2018.4.770

    Related Papers:

  • In recent years, conjugated polymers (CPs) and their nanoparticles (CPNs) were widely concerned and applied in many fields due to their outstanding advantages such as higher absorption coefficients, good photostability, low toxicity and good biocompatibility. However, most reports were focused on their applications, and rare attentions were given on the synthesis of CPs and the effect factors of CPNs’ morphology and properties. In this work, four CPs (P1, P2, P3, P4) with different length side chains were synthetized by Wittig–Horner reaction and further used to prepare CPNs by the nano-precipitation method. The CPs and CPNs were characterized and analyzed by Hydrogen Nuclear Magnetic Resonance (1H NMR), gel permeation chromatography (GPC), Fourier transform infrared spectroscopy (FTIR), dynamic light scattering (DLS) and transmission electron microscope (TEM). The absorbance and fluorescence emission spectra of CPs in tetrahydrofuran (THF) and CPNs solutions with different length side chains were investigated, and their quantum yields (Фs) were calculated by the reference method. The results showed that the synthetic CPs have narrow polydispersity index. Some interesting phenomenon appeared with the increased side chain length. The molecular weights will reduce except P3, and the absorbance and fluorescence emission spectra of CPs and CPNs are red-shifted. Фs are better and enlarged for CPs and CPNs, and better dispersion and uniform size were founded with longer side chains.


    加载中
    [1] Lyu Y, Pu K (2017) Recent advances of activatable molecular probes based on semiconducting polymer nanoparticles in sensing and imaging. Adv Sci 4: 1600481–1600487. doi: 10.1002/advs.201600481
    [2] Cui Q, Wang X, Yang Y, et al. (2016) Binding-directed energy transfer of conjugated polymer materials for dual-color imaging of cell membrane. Chem Mater 28: 4661–4669. doi: 10.1021/acs.chemmater.6b01424
    [3] Chan YH, Wu C, Ye F, et al. (2011) Development of ultrabright semiconducting polymer dots for ratiometric pH sensing. Anal Chem 83: 1448–1455. doi: 10.1021/ac103140x
    [4] Wu PJ, Chen JL, Chen CP, et al. (2013) Photoactivated ratiometric copper(II) ion sensing with semiconducting polymer dots. Chem Commun 49: 898–900. doi: 10.1039/C2CC37848E
    [5] Zhang P, Lu H, Chen H, et al. (2016) Cationic conjugated polymers-induced quorum sensing of bacteria cells. Anal Chem 88: 2985–2988. doi: 10.1021/acs.analchem.5b03920
    [6] Wu PJ, Kuo SY, Huang YC, et al. (2014) Polydiacetylene-enclosed near-infrared fluorescent semiconducting polymer dots for bioimaging and sensing. Anal Chem 86: 4831–4839. doi: 10.1021/ac404237q
    [7] Zhou X, Liang H, Jiang P, et al. (2016) Ultifunctional phosphorescent conjugated polymer dots for hypoxia imaging and photodynamic therapy of cancer cells. Adv Sci 3: 1500155–1500166. doi: 10.1002/advs.201500155
    [8] Palner M, Pu K, Shao S, et al. (2015) Semiconducting polymer nanoparticles with persistent near‐infrared luminescence for in vivo optical imaging. Angew Chem Int Edit 127: 11639–11642. doi: 10.1002/ange.201502736
    [9] Zhang D, Wu M, Zeng Y, et al. (2016) Lipid micelles packaged with semiconducting polymer dots as simultaneous MRI/photoacoustic imaging and photodynamic/photothermal dual-modal therapeutic agents for liver cancer. J Mater Chem B 4: 589–599. doi: 10.1039/C5TB01827G
    [10] Lyu Y, Xie C, Chechetka SA, et al. (2016) Semiconducting polymer nanobioconjugates for targeted photothermal activation of neurons. J Am Chem Sci 138: 9049–9052. doi: 10.1021/jacs.6b05192
    [11] Cai X, Liu X, Liao LD, et al. (2016) Encapsulated conjugated oligomer nanoparticles for real‐time photoacoustic sentinel lymph node imaging and targeted photothermal therapy. Small 12: 4873–4880. doi: 10.1002/smll.201600697
    [12] Cheng L, He W, Gong H, et al. (2013) PEGylated micelle nanoparticles encapsulating a non‐fluorescent near‐infrared organic dye as a safe and highly‐effective photothermal agent for in vivo cancer therapy. Adv Funct Mater 23: 5893–5902. doi: 10.1002/adfm.201301045
    [13] Li K, Liu B (2010) Water-soluble conjugated polymers as the platform for protein sensors. Polym Chem 1: 252–259. doi: 10.1039/B9PY00283A
    [14] Moon JH, McDaniel W, MacLean P, et al. (2007) Live‐cell‐permeable poly(p‐phenylene ethynylene). Angew Chem Int Edit 46: 8223–8225. doi: 10.1002/anie.200701991
    [15] Feng X, Yang G, Liu L, et al. (2012) A convenient preparation of multi‐spectral microparticles by bacteria‐mediated assemblies of conjugated polymer nanoparticles for cell imaging and barcoding. Adv Mater 24: 637–641. doi: 10.1002/adma.201102026
    [16] Khidre RE, Abdou WM (2016) Wittig–Horner reagents: powerful tools in the synthesis of 5- and 6-heterocyclic compounds; shedding light on their application in pharmaceutical chemistry. Turk J Chem 40: 225–247. doi: 10.3906/kim-1502-56
    [17] Wu C, Jin Y, Schneider T, et al. (2010) Ultrabright and bioorthogonal labeling of cellular targets using semiconducting polymer dots and click chemistry. Angew Chem Int Edit 49: 9436–9440. doi: 10.1002/anie.201004260
    [18] Wu C, Schneider T, Zeigler M, et al. (2010) Bioconjugation of ultrabright semiconducting polymer dots for specific cellular targeting. J Am Chem Sci 132: 15410–15417. doi: 10.1021/ja107196s
    [19] Wu C, Hansen SJ, Hou Q, et al. (2011) Design of highly emissive polymer dot bioconjugates for in vivo tumor targeting. Angew Chem Int Edit 50: 3430–3434. doi: 10.1002/anie.201007461
    [20] Li K, Pan J, Feng SS, et al. (2009) Generic strategy of preparing fluorescent conjugated‐polymer‐loaded poly(dl‐lactide‐co‐glycolide) nanoparticles for targeted cell imaging. Adv Funct Mater 19: 3535–3542. doi: 10.1002/adfm.200901098
    [21] Howes P, Green M, Levitt J, et al. (2010) Phospholipid encapsulated semiconducting polymer nanoparticles: their use in cell imaging and protein attachment. J Am Chem Sci 132: 3989–3996. doi: 10.1021/ja1002179
    [22] Yang G, Liu L, Yang Q, et al. (2012) A multifunctional cationic pentathiophene: Synthesis, organelle‐selective imaging, and anticancer activity. Adv Funct Mater 22: 736–743. doi: 10.1002/adfm.201101764
    [23] Ni D, Yang D, Ma S, et al. (2013) Side chains and backbone structures influence on 4,7-dithien-2-yl-2,1,3-benzothiadiazole (DTBT)-based low-bandgap conjugated copolymers for organic photovoltaics. Front Optoelectron 6: 418–428. doi: 10.1007/s12200-013-0343-9
    [24] Subramaniyan S, Xin H, Kim FS, et al. (2011) Effects of side chains on thiazolothiazole-based copolymer semiconductors for high performance solar cells. Adv Energy Mater 1: 854–860. doi: 10.1002/aenm.201100215
    [25] Zhang W, Shiotsuki M, Masuda T (2007) Synthesis and properties of polymer brush consisting of poly(phenylacetylene) main chain and poly(dimethylsiloxane) side chains. Polymer 48: 2548–2553. doi: 10.1016/j.polymer.2007.03.016
    [26] Zhu L, Jiang C, Chen G, et al. (2017) Side chain engineering: The effect on the properties of isoindigo-based conjugated polymers contain different length and structure alkyl chains on nitrogen atom. Org Electron 49: 278–285. doi: 10.1016/j.orgel.2017.06.035
    [27] Hwang KH, Kim DH, Min HC, et al. (2016) Effect of side chain position and conformation of quinacridone–quinoxaline based conjugated polymers on photovoltaic properties. J Ind Eng Chem 34: 66–75. doi: 10.1016/j.jiec.2015.10.029
    [28] Wang YJ, Larsson M, Huang WT, et al. (2016) The use of polymer-based nanoparticles and nanostructured materials in treatment and diagnosis of cardiovascular diseases: Recent advances and emerging designs. Prog Polym Sci 57: 153–178. doi: 10.1016/j.progpolymsci.2016.01.002
    [29] Kamaly N, Xiao Z, Valencia PM, et al. (2012) Targeted polymeric therapeutic nanoparticles: design, development and clinical translation. Chem Soc Rev 41: 2971–3010. doi: 10.1039/c2cs15344k
    [30] Razzellhollis J, Fleischli F, Jahnke AA, et al. (2017) Effects of side-chain length and shape on polytellurophene molecular order and blend morphology. J Phys Chem C 121: 11675–11679.
    [31] Duan C, Willems REM, Franeker JJV, et al. (2016) Effect of side chain length on the charge transport, morphology, and photovoltaic performance of conjugated polymers in bulk heterojunction solar cells. J Mater Chem A 4: 1855–1866. doi: 10.1039/C5TA09483F
    [32] Jiang YB, Gao C, Zhang X, et al. (2018) A highly selective and sensitive fluorescence probe with A-π-D-π-A structure for detection of Ag+. J Mol Struct 1163: 33–40. doi: 10.1016/j.molstruc.2018.01.058
    [33] Zhang X, Sun YM, Yu XQ, et al. (2009) Synthesis and nonlinear optical properties of several new two-photon photopolymerization initiators about dibenzothiophene derivatives. Synthetic Met 159: 2491–2496. doi: 10.1016/j.synthmet.2009.08.057
    [34] Shin CK, Lee H (2004) Effect of alkyl side-chain length and solvent on the luminescent characteristics of poly(3-n-alkylthiophene). Synthetic Met 140: 177–181. doi: 10.1016/S0379-6779(03)00361-8
    [35] Lecollinet G, Delorme N, Edely M, et al. (2009) Self-assembled monolayers of bisphosphonates: influence of side chain steric hindrance. Langmuir 25: 7828–7835. doi: 10.1021/la8039576
    [36] Meng XL, Zhang X, Yao JS, et al. (2013) Fluorescence and fluorescence imaging of two schiff derivatives sensitive to Fe3+ induced by single- and two-photon excitation. Sensor Actuat B-Chem 176: 488–496. doi: 10.1016/j.snb.2012.10.089
    [37] Fu B, Baltazar J, Sankar AR, et al. (2014) Enhancing field‐effect mobility of conjugated polymers through rational design of branched side chains. Adv Funct Mater 24: 3734–3744. doi: 10.1002/adfm.201304231
  • Reader Comments
  • © 2018 the Author(s), licensee AIMS Press. This is an open access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0)
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

Metrics

Article views(4293) PDF downloads(901) Cited by(4)

Article outline

Figures and Tables

Figures(6)  /  Tables(2)

/

DownLoad:  Full-Size Img  PowerPoint
Return
Return

Catalog