Synthesis of Novel Scolopendra-type Polydodecyloxybenzoyl[1, 5]-diazocine as New Material for Optical Sensor

Ya-Nan Liu; Jian-Zhong Li; Xiao-Bo Wan

doi:10.1007/s10118-018-2062-6

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Synthesis of Novel Scolopendra-type Polydodecyloxybenzoyl[1, 5]-diazocine as New Material for Optical Sensor

Articles | Updated：2021-02-18

- Synthesis of Novel Scolopendra-type Polydodecyloxybenzoyl[1, 5]-diazocine as New Material for Optical Sensor
- Synthesis of Novel Scolopendra-type Polydodecyloxybenzoyl[1, 5]-diazocine as New Material for Optical Sensor
- Chinese Journal of Polymer Science 2018年36卷第6期页码：736-741
- Affiliations：
  
  a.College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China
  b.Qingdao institute of Bioprocess Technology, Chinese Academy of Science, Qingdao 266101, China
- Author bio：
  
  E-mail jzhlee@163.com (J.Z.L.)
  E-mail wanxb@qibebt.ac.cn (X.B.W.)
- Funds：
- DOI：10.1007/s10118-018-2062-6
  中图分类号：
- 收稿：2017-09-01，
  
  录用：2017-10-11，
  
  网络首发：2018-02-08，
  
  纸质出版：2018-06
- Accepted：
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Ya-Nan Liu, Jian-Zhong Li, Xiao-Bo Wan. Synthesis of Novel Scolopendra-type Polydodecyloxybenzoyl[1, 5]-diazocine as New Material for Optical Sensor[J]. Chinese Journal of Polymer Science, 2018,36(6):736-741.

Ya-Nan Liu, Jian-Zhong Li, Xiao-Bo Wan. Synthesis of Novel Scolopendra-type Polydodecyloxybenzoyl[1, 5]-diazocine as New Material for Optical Sensor[J]. Chinese Journal of Polymer Science, 2018, 36(6): 736-741.
Ya-Nan Liu, Jian-Zhong Li, Xiao-Bo Wan. Synthesis of Novel Scolopendra-type Polydodecyloxybenzoyl[1, 5]-diazocine as New Material for Optical Sensor[J]. Chinese Journal of Polymer Science, 2018,36(6):736-741. DOI： 10.1007/s10118-018-2062-6.

Ya-Nan Liu, Jian-Zhong Li, Xiao-Bo Wan. Synthesis of Novel Scolopendra-type Polydodecyloxybenzoyl[1, 5]-diazocine as New Material for Optical Sensor[J]. Chinese Journal of Polymer Science, 2018, 36(6): 736-741. DOI： 10.1007/s10118-018-2062-6.

摘要

Abstract

A new scolopendra-type polymer of polydodecyloxybenzoyl[1

5]-diazocine (

PDBD

) was designed and prepared using 2

5-bis(4-(dodecyloxy)-benzoyl)terephthaloyl azide with trifluoroacetic acid (TFA)

via

one-pot reaction in good yields. The structure of polymer was characterized using

H-NMR

C-NMR and MALDI-TOF spectra. The polymer

PDBD

exhibits good thermal stability as measured by TGA and DSC

and can be dissolved well in common organic solvents such as chloroform and tetrahydrofuran. In addition

UV-Vis spectral studies indicate that the polymer

PDBD

shows unique optical property changes (protonation/deprotonation) in the different trifluoroacetic acid environments. The new polymer is expected to be utilized as an optical functional material for fabricating optical sensors in environmental and biological fields.

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Keywords

references

A. Sondheimer. . Zur kenntniss eines körpers mit achtgliedrigem ringe . Chem. Ber. , 1986 . 29 1272 - 1275 . https://onlinelibrary.wiley.com/doi/abs/10.1002/cber.18960290220 https://onlinelibrary.wiley.com/doi/abs/10.1002/cber.18960290220 , .

T. Suga , S. Wi , T. E. Long . Synthesis of diazocine-containing poly(arylene ether sulfone)s for tailored mechanical and electrochemical performance . Macromolecules , 2009 . 42 ( 5 ): 1526 - 1532 . DOI: 10.1021/ma802249a http://doi.org/10.1021/ma802249a .

S. Yoshida , A. S. Hay . Synthesis of all-aromatic phthalazinone-containing polymers by a novel N-C coupling reaction . Macromolecules , 1997 . 30 ( 8 ): 2254 - 2261 . DOI: 10.1021/ma961659l http://doi.org/10.1021/ma961659l .

J. J. Eisch , W. Liu , L. Zhu , A. L. Rheingold . Facile rearrangement of the 6, 11-diphenyldibenzo[b, f] [1, 4] diazocine skeleton into a substituted 2-(2-aminophenyl)-1, 3-diphenylisoindole via anomalous carbo-lithiation or hydrolithiation:corroboration of operative SET processes . Eur. J. Org. Chem. , 2015 . 33 7384 - 7374 . https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.201500917 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.201500917 , .

M. Bovenkerk , B. Esser . Synthesis of isoindoles by one-electron reductions of dibenzo[1, 4]diazocines . Eur. J. Org. Chem. , 2015 . 4 775 - 785 . https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.201403315 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.201403315 , .

X. Wang , J. Li , N. Zhao , X. Wan . A rapid and efficient access to diaryldibenzo[b, f][1, 5]diazocines . Org. Lett. , 2011 . 13 ( 4 ): 709 - 711 . DOI: 10.1021/ol102957c http://doi.org/10.1021/ol102957c .

N. Zhao , L. Qiu , X. Wang , J. Li , Y. Jiang , X. Wan . Trifluoroacetic acid catalyzed dibenzodiazocine synthesis:optimization and mechanism study . Tetrahedron , 2012 . 68 ( 47 ): 9665 - 9671 . DOI: 10.1016/j.tet.2012.09.050 http://doi.org/10.1016/j.tet.2012.09.050 .

C. Hoppin , R. B. Bates , C. G. Contreras , A. Somogyi , M. J. Streeter , H. K. Hall . Poly(dibenzodiazocine)s:analysis of low molecular weight fractions by MALDI-TOF MS . Polym. Bull. , 2009 . 63 ( 4 ): 509 - 515 . DOI: 10.1007/s00289-009-0118-z http://doi.org/10.1007/s00289-009-0118-z .

J. Li , X. Wan . Synthesis of novel polydiazocine for electroactive materials based on diazocine . J. Polym. Sci., Part A:Polym. Chem. , 2013 . 52 ( 21 ): 4694 - 4701 . https://onlinelibrary.wiley.com/doi/full/10.1002/pola.26891 https://onlinelibrary.wiley.com/doi/full/10.1002/pola.26891 , .

M. E. Lee , A. M. Armani . Flexible UV exposure sensor based on UV responsive polymer . ACS Sens. , 2016 . 1 1251 - 1255 . DOI: 10.1021/acssensors.6b00491 http://doi.org/10.1021/acssensors.6b00491 .

W. Shi , S. He , M. Wei , D. G. Evans , X. Duan . Optical pH sensor with rapid response based on a fluorescein-intercalated layered double hydroxide . Adv. Funct. Mater. , 2010 . 20 3856 - 3863 . DOI: 10.1002/adfm.201001081 http://doi.org/10.1002/adfm.201001081 .

S. Parola , B. Julián-López , L. D. Carlos , C. Sanchez . Optical properties of hybrid organic-inorganic materials and their applications . Adv. Funct. Mater. , 2016 . 26 6506 - 6544 . DOI: 10.1002/adfm.v26.36 http://doi.org/10.1002/adfm.v26.36 .

Q. Wang , L. Xiong , F. Zhu , L. Yang , G. Chang . High performance poly( N -aryleneindole ether) containing pyridine units as a novel acid response fluorescent detector . Polym. Int. , 2016 . 65 841 - 844 . https://onlinelibrary.wiley.com/doi/pdf/10.1002/pi.5145 https://onlinelibrary.wiley.com/doi/pdf/10.1002/pi.5145 , .

N. B. Borchert , G. V. Ponomarev , J. P. Kerry , D. B. Papkovsky . O 2 /pH multisensor based on one phosphorescent . Anal. Chem. , 2011 . 83 ( 1 ): 18 - 22 . DOI: 10.1021/ac1025754 http://doi.org/10.1021/ac1025754 .

F. Larisa , F. Cormac , L. Emer , P. Thomas , N. E. O'Connor , C. Brian . Dynamic pH mapping in microfluidic devices by integrating adaptive coatings based on polyaniline with colorimetric imaging techniques . Lab. Chip. , 2013 . 13 1079 - 1085 . DOI: 10.1039/c2lc41065f http://doi.org/10.1039/c2lc41065f .

E. Yuya , R. Hayashida , J. I. Anzai . Multilayered assemblies composed of brilliant yellow and poly(allylamine) for an optical pH sensor . Anal. Sci. , 2006 . 22 1117 - 1119 . DOI: 10.2116/analsci.22.1117 http://doi.org/10.2116/analsci.22.1117 .

T. Werner , C. Huber , S. Heinl , M. Kollmannsberger , J. Daub , O. S. Wolfbeis . Novel optical pH-sensor based on a boradiaza-indacene derivative . Fresenius J. Anal. Chem. , 1997 . 359 150 - 154 . DOI: 10.1007/s002160050552 http://doi.org/10.1007/s002160050552 .

W. Dorota , A. Tobias , M. Colette . Optical chemical pH sensors . Anal. Chem. , 2014 . 86 15 - 29 . DOI: 10.1021/ac4035168 http://doi.org/10.1021/ac4035168 .

A. M. Abo-Bakr , M. A. Hassan , H. H. Temirek , A. M. Mosallam . Synthesis of some new heterocyclic nitrogen compounds starting from pyromellitic dianhydride . Orient. J. Chem. , 2012 . 28 ( 4 ): 1567 - 1578 . DOI: 10.13005/ojc/280403 http://doi.org/10.13005/ojc/280403 .

K. Tsioris , G. E. Tilburey , A. R. Murphy , P. Domachuk , D. L. Kaplan , F. G. Omenetto . Functionalized-silk-based active optofluidic devices . Adv. Funct. Mater. , 2010 . 20 1083 - 1089 . DOI: 10.1002/adfm.v20:7 http://doi.org/10.1002/adfm.v20:7 .

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