A new kind of accordion-type chain-folded poly (ester urea) was designed and synthesized by polyesterfication of the monomer with dicarboxylic groups
4
4'-(carbonyldiimino) dibenzoic acid and the monomer with dibromo groups
3
5-bis (bromoalkoxyl) benzoate in polar solvents at ambient temperature. The kinetics of the polyesterification reaction was monitored by proton nuclear magnetic resonance (
1
H-NMR) tracking. It was found that the rate of the polyesterification was highly dependent on the length of the side alkyl chains in the monomer bearing dibromine groups. A shorter alkyl chain was more favorable for the polyestification owing to the different solubility of the monomers
the monomer bearing a long alkyl chain was more soluble. The number average molecular weight and the structure of the obtained poly (ester urea) were characterized by
1
H-NMR and Fourier transform infrared spectroscopy (FTIR). The number average molecular weight of the poly (ester urea) was measured to be about 2 × 10
4
. Differential scanning calorimetry (DSC) result showed that the melting point of the poly (ester urea) was 57 ℃
suggesting that the presence of crystallinity in the poly (ester urea). While the result from thermogravimetric analysis (TGA) displayed that the poly (ester urea) was highly thermal-stable with an obvious thermal degradation around 407 ℃. Because of the presence of the hydrogen-bond between the urea groups and
π-π
interaction between the phenyl units
self-assembly behavior of the poly (ester urea) in a mixed organic solvent of chloroform and methanol was characterized by transmission electron microscope (TEM). The result revealed that lamellar aggregates formed in the poly (ester urea) after self-assemble for 4 h. However
the lamellar aggregates ultimately transformed into thermodynamically stable vesicles after standing for 3 days. The thickness of the vesicle wall was estimated to be about 7 nm
close to the calculated size of the folded chain. Moreover
the result of X-ray diffraction (XRD) confirmed the presence of ordered structure in the polymer
demonstrating further that the poly (ester urea) adopts a chain-folded conformation.
C S Hartley . Acc Chem Res , 2016 . 49 646 - 654 . DOI:10.1021/acs.accounts.6b00038http://doi.org/10.1021/acs.accounts.6b00038.
D Siebler , M Linseis , T Gasi , L M Carrella , R F Winter , C Fçrster , K Heinze . Chem Eur J , 2011 . 17 4540 - 4551 . DOI:10.1002/chem.201002101http://doi.org/10.1002/chem.201002101.
D W Zhang , X Zhao , Z T Li . Acc Chem Res , 2014 . 47 1961 - 1970 . DOI:10.1021/ar5000242http://doi.org/10.1021/ar5000242.
R M Meudtner , M Ostermeier , R Goddard , C Limberg , S Hecht . Chem Eur J , 2007 . 13 9834 - 9840 . DOI:10.1002/chem.200701240http://doi.org/10.1002/chem.200701240.
K Liu , X Zheng , A Z Samuel , S G Ramkumar , S Ghosh , X Tan , D Wang , Z Shuai , S Ramakrishnan , D S Liu . Langmuir , 2013 . 29 14438 - 14443 . DOI:10.1021/la403709uhttp://doi.org/10.1021/la403709u.
T Kunitake , N Nakashima , K Takarabe , M Nagai , A Tsuge , H Yanagi . J Am Chem Soc , 1981 . 103 5945 - 5941 . DOI:10.1021/ja00409a071http://doi.org/10.1021/ja00409a071.
Y Suzuki , S Tazuke . Macromolecules , 1980 . 13 25 - 30 . DOI:10.1021/ma60073a005http://doi.org/10.1021/ma60073a005.
Y Suzuki , S Tazuke . Macromolecules , 1981 . 14 1742 - 1747 . DOI:10.1021/ma50007a025http://doi.org/10.1021/ma50007a025.
J D Hong , B D Jung , C H Kim , K Kim . Macromolecules , 2000 . 33 7905 - 7911 . DOI:10.1021/ma000293ghttp://doi.org/10.1021/ma000293g.
S De , S Ramakrishnan . Macromolecules , 2009 . 42 8599 - 8603 . DOI:10.1021/ma901954xhttp://doi.org/10.1021/ma901954x.
R K Roy , E B Gowd , S Ramakrishnan . Macromolecules , 2012 . 45 3063 - 3069 . DOI:10.1021/ma2023414http://doi.org/10.1021/ma2023414.
Mandal Joydeb , S Krishna Prasad , D S Shankar Rao , S Ramakrishnan . J Am Chem Soc , 2014 . 136 2538 - 2545 . DOI:10.1021/ja411583fhttp://doi.org/10.1021/ja411583f.
Q B Li , Y Y Bao , H Wang , F F Du , Q Li , B K Jin , R K Bai . Polym Chem , 2013 . 4 2891 - 2897 . DOI:10.1039/c3py00155ehttp://doi.org/10.1039/c3py00155e.
Q B Li , T S Wang , C Ma , W Bai , R K Bai . ACS Macro Lett , 2014 . 3 1161 - 1164 . DOI:10.1021/mz5005184http://doi.org/10.1021/mz5005184.
M I Helen , Osborn , O Nana Aba . Organic Letters , 2004 . 6 3111 - 3113 . DOI:10.1021/ol040042ihttp://doi.org/10.1021/ol040042i.
E Filali , G C Lloyd-Jones , D A Sale . Synlett , 2009 . 2 205 - 208.
J Li , D M Zhang , X Zhu , Z J He , S Liu , M F Li , J Y Pang , Y C Lin . Mar Drugs , 2011 . 9 1887 - 1901 . DOI:10.3390/md9101887http://doi.org/10.3390/md9101887.
Fang Huagao (方高华). Preparation, Structural Characterization and Properties of Long Chain Branched Polyactides and Toughened Polyactide Blends (长链支化聚乳酸和增韧改性聚乳酸共混物的制备、结构表征及性能研究). Doctoral Dissertation of University of Science and Technology of China (中国科学技术大学博士学位论文), 2014
J Y Gao , M Z Wang , F Y K Wang , J Z Du . Biomacromolecules , 2016 . 17 2080 - 2086 . DOI:10.1021/acs.biomac.6b00307http://doi.org/10.1021/acs.biomac.6b00307.
B Yu , X S Jiang , J Yin . Macromolecules , 2014 . 47 4761 - 4768 . DOI:10.1021/ma500845ehttp://doi.org/10.1021/ma500845e.
Y B Ruan , L Gao , D D Yao , K Zhang , Y M Chen , C Y Liu . ACS Macro Lett , 2015 . 4 1067 - 1071 . DOI:10.1021/acsmacrolett.5b00408http://doi.org/10.1021/acsmacrolett.5b00408.
Wei Deng , Yonghong Deng , Xiaogong Wang . Acta Polymerica Sinica , 2009 . ( 2 ): 128 - 133 . http://www.gfzxb.org/CN/abstract/abstract12287.shtml.
G Li , F F Du , H Wang , R K Bai . React Funct Polym , 2014 . 75 75 - 80 . DOI:10.1016/j.reactfunctpolym.2013.12.007http://doi.org/10.1016/j.reactfunctpolym.2013.12.007.
X J Ma , Y B Zhang , Y F Zhang , C Peng , Y K Che , J C Zhao . Adv Mater , 2015 . 27 7746 - 7751 . DOI:10.1002/adma.201503771http://doi.org/10.1002/adma.201503771.
Y Q Zhu , L Fang , B Yang , J Z Du . ACS Nano , 2014 . 8 5022 - 5031 . DOI:10.1021/nn5010974http://doi.org/10.1021/nn5010974.
Y Q Zhu , B Yang , S Chen , J Z Du . Prog Polym Sci , 2017 . 64 1 - 22 . DOI:10.1016/j.progpolymsci.2015.05.001http://doi.org/10.1016/j.progpolymsci.2015.05.001.
M Z Wang , T Wang , K Yuan , J Z Du . Chinese J Polym Sci , 2016 . 34 44 - 51 . DOI:10.1007/s10118-016-1725-4http://doi.org/10.1007/s10118-016-1725-4.
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