Supramolecular ordered photochromic cholesteric polymers as smart labels for thermal monitoring applications

Dyes and Pigments

Volumn 126, Issue , 2016, Pages 8-19

  Benelli, Tiziana ^a   Mazzocchetti, Laura ^a   Mazzotti, Giovanni ^a   Paris, Fabio ^a   Salatelli, Elisabetta ^a   Giorgini, Loris ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Atom transfer radical polymerization; Chirality; Cholesteric polymers; Liquid crystals; Supramolecular chemistry; Temperature sensitive tag

Indexed keywords

CHEMICAL REACTIONS; CHIRALITY; CHOLESTERIC LIQUID CRYSTALS; CHROMOPHORES; FILMS; FREE RADICAL REACTIONS; LABELS; LASER OPTICS; LIQUID CRYSTALS; POLYMERIZATION; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY; THICK FILMS;

AZOAROMATIC CHROMOPHORE; CONFORMATIONAL ORDER; CONTROLLED RADICAL POLYMERIZATION; MILD REACTION CONDITIONS; PERISHABLE COMMODITIES; POLYMER MOLECULAR WEIGHT; TEMPERATURE SENSITIVE; TRANS-CIS ISOMERIZATION;

ATOM TRANSFER RADICAL POLYMERIZATION;

EID: 84949309250     PISSN: 01437208     EISSN: 18733743     Source Type: Journal    
DOI: 10.1016/j.dyepig.2015.11.009     Document Type: Article

References (51)

1. Matacotta FC, Biscarini F, Cavallini M, Stoliar PA. System and method for authenticating products and/or packages. US Patent 20100008561 A1. 2010.
2. Biscarini F, Cavallini M, Matacotta FC, Greco P, Lanza S, Mattiazzi P, et al. Flexible reading device for traceability of products. US Patent 8558206 B2. 2013.
3. Cavallini M, Biscarini F, Matacotta FC, Stoliar PA. Device and method for monitoring the temperature to which a product has been exposed. US Patent 20090123334 A1. 2009.
4. K.L. Yam, P.T. Takhistov, and J. Miltz Intelligent packaging: concepts and applications J Food Sci 70 2005 R1 R10
5. Seiter C. Time-temperature indicator. US Patent 4057029. 1977. US.
6. William W, Campbell LB. Temperature indicator. US Patent 3002385 A. 1961.
7. Gregory OJ, McCauley JJ. Method utilizing a ceramic for temperature measurement. US Patent 5338566 A. 1994. US.
8. Preziosi AF, Prusik T, Baughman RH. Defrost indicator. US Patent 4892677 A. 1990.
9. Boyaci IH, Torun O, Ozbalci B. Intelligent temperature indicator label and method. US Patent 8695528 B2. 2014.
10. D. Galliani, L. Mascheroni, M. Sassi, R. Turrisi, R. Lorenzi, A. Scaccabarozzi, and et al. Thermochromic latent-pigment-based time-temperature indicators for perishable goods Adv Opt Mater 3 2015 1164 1168
11. A. Seeboth, D. Lötzsch, R. Ruhmann, and O. Muehling Thermochromic polymers - function by design Chem Rev 114 2014 3037 3068
12. A. Seeboth, and D. Lötzsch Thermochromic polymers, encyclopedia of polymer science and technology 2002 John Wiley & Sons, Inc.
13. T. Kajitani, H. Masu, S. Kohmoto, M. Yamamoto, K. Yamaguchi, and K. Kishikawa Generation of a chiral mesophase by achiral molecules: absolute chiral induction in the smectic C phase of 4-octyloxyphenyl 4-octyloxybenzoate J Am Chem Soc 127 2005 1124 1125
14. L. Angiolini, T. Benelli, L. Giorgini, and E. Salatelli Optically active photochromic methacrylic polymers with controlled average molecular weight and defined end-groups by atom transfer radical polymerization Polymer 46 2005 2424 2432
15. T. Kaneko, Y. Umeda, T. Yamamoto, M. Teraguchi, and T. Aoki Assignment of helical sense for poly(phenylacetylene) bearing achiral galvinoxyl chromophore synthesized by helix-sense-selective polymerization Macromolecules 38 2005 9420 9426
16. B.L. Feringa, R.A. van Delden, N. Koumura, and E.M. Geertsema Chiroptical molecular switches Chem Rev 100 2000 1789 1816
17. L. Angiolini, T. Benelli, L. Giorgini, E. Salatelli, R. Bozio, A. Daurù, and et al. Synthesis, chiroptical properties and photoinduced linear birefringence of the homopolymer of (R)-3-methacryloyloxy-1-(4′-cyano-4-azobenzene) pyrrolidine and of the copolymers with the enantiomeric monomer Eur Polym J 41 2005 2045 2054
18. J. Barberá, L. Giorgini, F. Paris, E. Salatelli, R.M. Tejedor, and L. Angiolini Supramolecular chirality and reversible chiroptical switching in new chiral liquid-crystal azopolymers Chem A Eur J 14 2008 11209 11221
19. L. Angiolini, T. Benelli, L. Giorgini, F. Mauriello, and E. Salatelli Chiroptical and optical thermoplastic acid sensors based on chiral methacrylic polymers containing azoaromatic moieties Sens Actuators B Chem 126 2007 56 61
20. M. Liu, L. Zhang, and T. Wang Supramolecular chirality in self-assembled systems Chem Rev 2015
21. K. Ichimura Photoalignment of liquid-crystal systems Chem Rev 100 2000 1847 1874
22. V. Shibaev, A. Bobrovsky, and N. Boiko Photoactive liquid crystalline polymer systems with light-controllable structure and optical properties Prog Polym Sci 28 2003 729 836
23. S. Chandrasekhar Liquid crystals 1993 Cambridge University Press New York
24. A. Bobrovsky, N. Boiko, and V. Shibaev Kinetics of helix untwisting in photosensitive cholesteric polymer mixtures: influence of molecular mass and ordered phase formation Macromolecules 39 2006 6367 6370
25. K. Matyjaszewski, P.J. Miller, J. Pyun, G. Kickelbick, and S. Diamanti Synthesis and characterization of Star polymers with varying arm number, length, and composition from organic and hybrid inorganic/organic multifunctional initiators Macromolecules 32 1999 6526 6535
26. L. Angiolini, T. Benelli, L. Giorgini, and E. Salatelli Optically active photochromic polymers with three-arm star structure by atom transfer radical polymerization Macromolecules 39 2006 3731 3737
27. A.S. Angeloni, D. Caretti, M. Laus, E. Chiellini, and G. Galli Mesomorphic polyacrylates containing isomeric methyl-substituted azobenzene mesogens J Polym Sci A Polym Chem 29 1991 1865 1873
28. P.J. Shannon Synthesis of methacrylate and acrylate monomers of cholesteric esters via phase transfer catalysis Macromolecules 16 1983 1677 1678
29. G.J.P. Britovsek, J. England, and A.J.P. White Non-heme iron(II) complexes containing tripodal tetradentate nitrogen ligands and their application in alkane oxidation catalysis Inorg Chem 44 2005 8125 8134
30. W.L.F. Armarego, and D.D. Perrin Purification of laboratory chemicals 1966 Pergamon Press Oxford
31. J. Xia, and K. Matyjaszewski Controlled/"Living" radical polymerization. Homogeneous reverse atom transfer radical polymerization using AIBN as the initiator Macromolecules 30 1997 7692 7696
32. K. Matyjaszewski, and J. Xia Atom transfer radical polymerization Chem Rev 101 2001 2921 2990
33. P.J. Shannon Photopolymerization in cholesteric mesophases Macromolecules 17 1984 1873 1876
34. H.H. Jaffé, and M. Orchin Theory and application of ultraviolet spectroscopy 1962 John Wiley New York
35. I. Zebger, M. Rutloh, U. Hoffmann, J. Stumpe, H.W. Siesler, and S. Hvilsted Photoorientation of a liquid-crystalline polyester with azobenzene side groups: effects of irradiation with linearly polarized red light after photochemical pretreatment Macromolecules 36 2003 9373 9382
36. S.W. Choi, S. Kawauchi, N.Y. Ha, and H. Takezoe Photoinduced chirality in azobenzene-containing polymer systems Phys Chem Chem Phys 9 2007 3671 3682
37. D. Hore, Y.L. Wu, A. Natansohn, and P. Rochon Investigation of circular Bragg reflection in an azo polymer with photoinduced chirality J Appl Phys 94 2003 2162 2166
38. R.M. Tejedor, M. Millaruelo, L. Oriol, J.L. Serrano, R. Alcala, F.J. Rodriguez, and et al. Photoinduced supramolecular chirality in side-chain liquid crystalline azopolymers J Mater Chem 16 2006 1674 1680
39. R.M. Tejedor, L. Oriol, J.L. Serrano, F. Partal Ureña, and J.J. López González Photoinduced chiral nematic organization in an achiral glassy nematic azopolymer Adv Funct Mater 17 2007 3486 3492
40. L. Angiolini, J. Barberá, T. Benelli, L. Giorgini, F. Paris, E. Salatelli, and et al. Photoinduced supramolecular chirality in glassy nematic linear and star shaped methacrylic azopolymers obtained by ATRP E-Polymers 2009 045
41. F.D. Saeva, and J.J. Wysocki Induced circular dichroism in cholesteric liquid crystals J Am Chem Soc 93 1971 5928 5929
42. I. Chabay Absorptive and scattering circular dischroism of cholesteric liquid crystals in the infrared Chem Phys Lett 17 1972 283 287
43. F.D. Saeva Cholesteric liquid-crystal-induced circular dichroism (LCICD) of achiral solutes. Novel spectroscopic technique J Am Chem Soc 94 1972 5135 5136
44. E. Sackmann, and J. Voss Circular dichroism of helically arranged molecules in cholesteric phases Chem Phys Lett 14 1972 528 532
45. S. Kurihara, S. Nomiyama, and T. Nonaka Photochemical control of the macrostructure of cholesteric liquid crystals by means of photoisomerization of chiral azobenzene molecules Chem Mater 13 2001 1992 1997
46. A. Bobrovsky, V. Shibaev, V. Hamplova, M. Kaspar, and M. Glogarova Chirooptical and photooptical properties of a novel side-chain azobenzene-containing LC polymer Monatsh fur Chem 140 2009 789 799
47. H. Stegemeyer, H. Onusseit, and H. Finkelmann Formation of a blue phase in a liquid-crystalline side chain polysiloxane Makromol Chem Rapid Commun 10 1989 571 574
48. J.M. Gilli, M. Kamaye, and R. Sixou Phases bleues "figées" dans un polysiloxane mésomorphe J Phys 50 1989 2911 2918
49. J.M. Gilli, M. Kamaye, and P. Sixou Quenched blue phase, below the glass transition of a side chain polysiloxane: electron microscope studies Mol Cryst Liq Cryst 199 1991 79 86
50. H. Stegemeyer, T.H. Blumel, K. Hiltrop, H. Onusseit, and F. Porsch Thermodynamic, structural and morphological studies on liquid-crystalline blue phases Liq Cryst 1 1986 3 28
51. E. Demikhov, and H. Stegemeyer Spatial dispersion in chiral liquid crystals. Effects of higher orders Liq Cryst 14 1993 1801 1830