Citation: Lei Zhang, Yi-Zhong Yuan, Xiao-Hui Tian, Jin-Yu Sun. A thermally reversible supramolecular system based on biphenyl polydiacetylene[J]. Chinese Chemical Letters, ;2015, 26(9): 1133-1136. doi: 10.1016/j.cclet.2015.05.027 shu

A thermally reversible supramolecular system based on biphenyl polydiacetylene

Lei Zhang ² ,
Yi-Zhong Yuan ^2,, ,
Xiao-Hui Tian ^1,2,, ,
Jin-Yu Sun ²

1.
1 Key Laboratory of Ultrafine Materials of Ministry of Education, East China University of Science and Technology, Shanghai 200237, China;
2.
2 Shanghai Key Laboratory of Advanced Polymeric Materials, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China

Corresponding author: Yi-Zhong Yuan, Xiao-Hui Tian,
Received Date: 18 March 2015
Available Online: 11 May 2015
Fund Project: the Fundamental Research Funds for the Central Universities (No. 22A201514002). (863 program)

A new type of diacetylene monomer which includes a biphenylcarboxylic acid group as its head group is synthesized. Polymerization was performed after monomer form spherical vesicle by self-assembly in the water. The polydiacetylene displayed completely thermochromic color change in the range of 20-95℃ owing to the presence of strong π-π interaction caused by biphenyl group and hydrogen bonding between head group.
- Polydiacetylene,
- Head group,
- Self-assembly,
- Reversible
1. [1]
  [1] X.R. Duan, L.B. Liu, F.D. Feng, S. Wang, Cationic conjugated polymers for optical detection of DNA methylation, lesions, and single nucleotide polymorphisms, Acc. Chem. Res. 43(2010) 260-270.
2. [2]
  [2] S. Günes, H. Neugebauer, N.S. Sariciftci, Conjugated polymer-based organic solar cells, Chem. Rev. 107(2007) 1324-1388.
3. [3]
  [3] F. Hide, M.A. Díaz-García, B.J. Schwartz, A.J. Heeger, New developments in the photonic applications of conjugated polymers, Acc. Chem. Res. 30(1997) 430-436.
4. [4]
  [4] X.L. Feng, L.B. Liu, S. Wang, D.B. Zhu, Water-soluble fluorescent conjugated polymers and their interactions with biomacromolecules for sensitive biosensors, Chem. Soc. Rev. 39(2010) 2411-2419.
5. [5]
  [5] H.N. Kim, Z.Q. Guo, W.H. Zhu, J. Yoon, H. Tian, Recent progress on polymer-based fluorescent and colorimetric chemosensors, Chem. Soc. Rev. 40(2011) 79-93.
6. [6]
  [6] X.Q. Chen, G.D. Zhou, X.J. Peng, J. Yoon, Biosensors and chemosensors based on the optical responses of polydiacetylenes, Chem. Soc. Rev. 41(2012) 4610-4630.
7. [7]
  [7] S.W. Thomas III, G.D. Joly, T.M. Swager, Chemical sensors based on amplifying fluorescent conjugated polymers, Chem. Rev. 107(2007) 1339-1386.
8. [8]
  [8] X.M. Sun, T. Chen, S.Q. Huang, L. Li, H.S. Peng, Chromatic polydiacetylene with novel sensitivity, Chem. Soc. Rev. 39(2010) 4244-4257.
9. [9]
  [9] D.H. Charych, J.O. Nagy, W. Spevak, M.D. Bendnarski, Direct colorimetric detection of a receptor-ligand interaction by a polymerized bilayer assembly, Science 261(1993) 585-588.
10. [10]
  [10] A. Herland, O. Inganäs, Conjugated polymers as optical probes for protein interactions and protein conformations, Macromol. Rapid Commun. 28(2007) 1703-1713.
11. [11]
  [11] S. Okada, S. Peng, W. Spevak, D. Charych, Color and chromism of polydiacetylene vesicles, Acc. Chem. Res. 31(1998) 229-239.
12. [12]
  [12] C.H. Fan, K.W. Plaxco, A.J. Heeger, High-efficiency fluorescence quenching of conjugated polymers by proteins, J. Am. Chem. Soc. 124(2002) 5642-5643.
13. [13]
  [13] D.J. Ahn, J.-M. Kim, Fluorogenic polydiacetylene supramolecules:immobilization, micropatterning, and application to label-free chemosensors, Acc. Chem. Res. 41(2008) 805-816.
14. [14]
  [14] D. Day, H. Ringsdorf, Polymerization of diacetylene carbonic acid monolayers at the gas-water interface, J. Polym. Sci. Polym. Lett. Ed. 16(1978) 205-210.
15. [15]
  [15] Y. Okawa, M. Aono, Nanoscale control of chain polymerization, Nature 409(2001) 683-684.
16. [16]
  [16] R. Jelinek, S. Kolusheva, Polymerized lipid vesicles as colorimetric biosensors for biotechnological applications, Biotechnol. Adv. 19(2001) 109-118.
17. [17]
  [17] O. Endo, H. Ootsubo, N. Toda, et al., Phase transition of a single sheet of sashlike polydiacetylene atomic sash on a solid surface, J. Am. Chem. Soc. 126(2004) 9894-9895.
18. [18]
  [18] J.M. Schnur, B.R. Ratna, J.V. Selinger, et al., Diacetylenic lipid tubules:experimental evidence for a chiral molecular architecture, Science 264(1994) 945-947.
19. [19]
  [19] J. Song, J.S. Cisar, C.R. Bertozzi, Functional self-assembling bolaamphiphilic polydiacetylenes as colorimetric sensor scaffolds, J. Am. Chem. Soc. 126(2004) 8459-8465.
20. [20]
  [20] D.J. Ahn, E.H. Chae, G.S. Lee, et al., Colorimetric reversibility of polydiacetylene supramolecules having enhanced hydrogen-bonding under thermal and pH stimuli, J. Am. Chem. Soc. 125(2003) 8976-8977.
21. [21]
  [21] S. Dei, T. Shimogaki, A. Matsumoto, Thermochromism of polydiacetylenes containing robust 2D hydrogen bond network of naphthylmethylammonium carboxylates, Macromolecules 41(2008) 6055-6065.
22. [22]
  [22] S.Y. Lee, Y.Y. Cho, B.U. Ye, et al., Unprecedented colorimetric responses of polydiacetylenes driven by plasma induced polymerization and their patterning applications, Chem. Commun. 50(2014) 12447-12449.
23. [23]
  [23] S.Y. Lee, J.Y. Lee, H.N. Kim, M.H. Kim, J.Y. Yoon, Thermally reversible polydiacetylenes derived from ethylene oxide-containing bisdiacetylenes, Sens. Actuators B 173(2012) 419-425.
24. [24]
  [24] C.A. Sandstedt, C.J. Eckhardt, M.J. Downey, D.J. Sandman, Optical, calorimetric, and mass spectroscopic study of nonthermochromic crystalline forms of the polydiacetylene bis(ethylurethane)-5,7-dodecadiyne-1,12-diol (ETCD), Chem. Mater. 6(1994) 1346-1350.
25. [25]
  [25] R.R. Chance, Chromism in polydiacetylene solutions and crystals, Macromolecules 13(1980) 396-398.
26. [26]
  [26] A.D. Nava, M. Thakur, A.E. Tonelli, Carbon-13 NMR structural studies of a soluble polydiacetylene, poly(4BCMU), Macromolecules 23(1990) 3055-3063.
27. [27]
  [27] Y. Tomioka, N. Tanaka, S. Imazeki, Effects of side-group interactions on pressureinduced chromism of polydiacetylene monolayer at a gas-water interface, Thin Solid Films 179(1989) 27-31.
28. [28]
  [28] R.W. Carpick, D.Y. Sasaki, A.R. Burns, First observation of mechanochromism at the nanometer scale, Langmuir 16(2000) 1270-1278.
29. [29]
  [29] R.A. Nallicheri, M.F. Rubner, Investigations of the mechanochromic behavior of poly(urethane-diacetylene) segmented copolymers, Macromolecules 24(1991) 517-525.
30. [30]
  [30] C.G. Wang, Z.F. Ma, Colorimetric detection of oligonucleotides using a polydiacetylene vesicle sensor, Anal. Bioanal. Chem. 382(2005) 1708-1710.
31. [31]
  [31] A. Reichert, J.O. Nagy, W. Spevak, D. Charych, Polydiacetylene liposomes functionalized with sialic acid bind and colorimetrically detect influenza virus, J. Am. Chem. Soc. 117(1995) 829-830.
32. [32]
  [32] Q. Cheng, R.C. Stevens, Coupling of an induced fit enzyme to polydiacetylene thin films:colorimetric detection of glucose, Adv. Mater. 9(1997) 481-483.
33. [33]
  [33] C. Phollookin, S. Wacharasindhu, A. Ajavakom, et al., Tuning down of color transition temperature of thermochromically reversible bisdiynamide polydiacetylenes, Macromolecules 43(2010) 7540-7548.
34. [34]
  [34] X.Q. Chen, J.Y. Yoon, A thermally reversible temperature sensor based on polydiacetylene:synthesis and thermochromic properties, Dyes Pigments 89(2011) 194-198.
35. [35]
  [35] J.-M. Kim, J.S. Lee, H. Choi, D. Sohn, D.J. Ahn, Rational design and in-situ FTIR analyses of colorimetrically reversible polydiacetylene supramolecules, Macromolecules 38(2005) 9366-9376.
36. [36]
  [36] L. Yu, S.L. Hsu, A spectroscopic analysis of the role of side chains in controlling thermochromic transitions in polydiacetylenes, Macromolecules 45(2012) 420-429.
37. [37]
  [37] S.Y. Lee, J.S. Lee, J.Y. Yoon, et al., Construction and molecular understanding of an unprecedented, reversibly thermochromic bis-polydiacetylene, Adv. Funct. Mater. 24(2014) 3699-3705.
1. [1]
  Zhiqing Ge , Zuxiong Pan , Shuo Yan , Baoying Zhang , Xiangyu Shen , Mozhen Wang , Xuewu Ge . Novel high-temperature thermochromic polydiacetylene material and its application as thermal indicator. Chinese Chemical Letters, 2024, 35(11): 109850-. doi: 10.1016/j.cclet.2024.109850
2. [2]
  Yang Qin , Jiangtian Li , Xuehao Zhang , Kaixuan Wan , Heao Zhang , Feiyang Huang , Limei Wang , Hongxun Wang , Longjie Li , Xianjin Xiao . Toeless and reversible DNA strand displacement based on Hoogsteen-bond triplex. Chinese Chemical Letters, 2024, 35(5): 108826-. doi: 10.1016/j.cclet.2023.108826
3. [3]
  Yuanpeng Ye , Longfei Yao , Guofeng Liu . Engineering circularly polarized luminescence through symmetry manipulation in achiral tetraphenylpyrazine structures. Chinese Journal of Structural Chemistry, 2025, 44(2): 100460-100460. doi: 10.1016/j.cjsc.2024.100460
4. [4]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
5. [5]
  Yuwen Zhu , Xiang Deng , Yan Wu , Baode Shen , Lingyu Hang , Yuye Xue , Hailong Yuan . Formation mechanism of herpetrione self-assembled nanoparticles based on pH-driven method. Chinese Chemical Letters, 2025, 36(1): 109733-. doi: 10.1016/j.cclet.2024.109733
6. [6]
  Jingqi Xin , Shupeng Han , Meichen Zheng , Chenfeng Xu , Zhongxi Huang , Bin Wang , Changmin Yu , Feifei An , Yu Ren . A nitroreductase-responsive nanoprobe with homogeneous composition and high loading for preoperative non-invasive tumor imaging and intraoperative guidance. Chinese Chemical Letters, 2024, 35(7): 109165-. doi: 10.1016/j.cclet.2023.109165
7. [7]
  Keyang Li , Yanan Wang , Yatao Xu , Guohua Shi , Sixian Wei , Xue Zhang , Baomei Zhang , Qiang Jia , Huanhua Xu , Liangmin Yu , Jun Wu , Zhiyu He . Flash nanocomplexation (FNC): A new microvolume mixing method for nanomedicine formulation. Chinese Chemical Letters, 2024, 35(10): 109511-. doi: 10.1016/j.cclet.2024.109511
8. [8]
  Xuanyu Wang , Zhao Gao , Wei Tian . Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction. Chinese Chemical Letters, 2024, 35(11): 109757-. doi: 10.1016/j.cclet.2024.109757
9. [9]
  Xian Yan , Huawei Xie , Gao Wu , Fang-Xing Xiao . Boosted solar water oxidation steered by atomically precise alloy nanocluster. Chinese Chemical Letters, 2025, 36(1): 110279-. doi: 10.1016/j.cclet.2024.110279
10. [10]
  Feng Cao , Chunxiang Xian , Tianqi Yang , Yue Zhang , Haifeng Chen , Xinping He , Xukun Qian , Shenghui Shen , Yang Xia , Wenkui Zhang , Xinhui Xia . Gelation-pyrolysis strategy for fabrication of advanced carbon/sulfur cathodes for lithium-sulfur batteries. Chinese Chemical Letters, 2025, 36(3): 110575-. doi: 10.1016/j.cclet.2024.110575
11. [11]
  Fengying Ye , Ming Hu , Jun Luo , Wei Yu , Zhirong Xu , Jinjin Fu , Yansong Zheng . Significantly boosting circularly polarized luminescence by synergy of helical and planar chirality. Chinese Chemical Letters, 2025, 36(5): 110724-. doi: 10.1016/j.cclet.2024.110724
12. [12]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
13. [13]
  Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
14. [14]
  Changlin Su , Wensheng Cai , Xueguang Shao . Water as a probe for the temperature-induced self-assembly transition of an amphiphilic copolymer. Chinese Chemical Letters, 2025, 36(4): 110095-. doi: 10.1016/j.cclet.2024.110095
15. [15]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
16. [16]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
17. [17]
  Fengyao Cui , Qiaona Zhang , Tangxin Xiao , Zhouyu Wang , Leyong Wang . Reversible phosphorescence in pseudopolyrotaxane elastomer. Chinese Chemical Letters, 2024, 35(10): 110061-. doi: 10.1016/j.cclet.2024.110061
18. [18]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
19. [19]
  Ruoxi Sun , Yiqian Xu , Shaoru Rong , Chunmiao Han , Hui Xu . The Enchanting Collision of Light and Time Magic: Exploring the Footprints of Long Afterglow Lifetime. University Chemistry, 2024, 39(5): 90-97. doi: 10.3866/PKU.DXHX202310001
20. [20]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(809)
HTML views(11)

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