Fulgide dyes

References

1. Stobbe H. Die farbigen Anhydride der Butadiën-β,γ-dicarbonsäuren; ihr Verhalten gegen Licht und Warme (II. Abhandlung über Butadiënverbindungen.). Ber Deutschen Chemischen Ges. 1904;37:2236–40.10.1002/cber.190403702159Search in Google Scholar

2. Stobbe H. Die Farbe der »Fulgensäuren« und »Fulgide« (7. Abhandlung über Butandiënverbindungen.). Ber Deutschen Chemischen Ges. 1905;38:3673–82.10.1002/cber.190503803214Search in Google Scholar

3. Yokoyama Y, Kurita Y. Photochromism of fulgides and related compounds. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst. 1994;246:87–94.10.1080/10587259408037793Search in Google Scholar

4. Heller HG. Electronic materials: from silicon to organics. Miller LS, Mullin JB, editors. New York: Springer, 1991 Chapter 31 (“Photochromics for the future”):471–83.10.1007/978-1-4615-3818-9_31Search in Google Scholar

5. Fan MG, Yu L, Zhao W. In: Crano JC, Guglielmetti RJ, editors. Organic photochromic and thermochromic compounds volume 1: main photochromic families. New York: Plenum, 1999 Chapter 4 (“Fulgide family compounds: synthesis, photochromism and applications”):141–206.10.1007/0-306-46911-1_5Search in Google Scholar

6. Yokoyama Y. Fulgides for memories and switches. Chem Rev. 100:1717–39.10.1021/cr980070cSearch in Google Scholar

7. Whittal J. In: Dürr H, Bouas-Laurent H editors. Photochromism molecules and systems . Amsterdam: Elsevier, 2003 Chapter 9 (“4n+2 Systems: Fulgides”):467–92.10.1016/B978-044451322-9/50013-0Search in Google Scholar

8. Mustroph H. Polymethine dyes. Phys Sci Rev. 2020;5. DOI:doi.org/10.1515/psr-2019-0084.Search in Google Scholar

9. Uhlmann E, Gauglitz G. New aspects in the photokinetics of Aberchrome 540. J Photochem Photobiol A: Chem. 1996;98:45–9.10.1016/1010-6030(96)04323-7Search in Google Scholar

10. Renth F, Siewertsen R, Temps F. Enhanced photoswitching and ultrafast dynamics in structurally modified photochromic fulgides. Int Rev Phys Chem. 2013;32:1–38.10.1080/0144235X.2012.729331Search in Google Scholar

11. Kaftory M. Photochromic and thermochromic compounds. I. Structures of (E) and (Z) isomers of 2-isopropylidene-3-[1-(2-methyl-5-phenyl-3-thienyl)ethylidene]succinic anhydride, C20H18O3S, and the photoproduct 7,7a-dihydro-4,7,7,7a-tetramethyl-2-phenylbenzo[b]thiophene-5,6-dicarboxylic anhydride (P), C20H18O3S. Acta Cryst. 1984;C40:1015–19.10.1107/S0108270184006624Search in Google Scholar

12. Hettiarachchi CV, Weerasekara RK, Uekusa H. Crystalline state photochromism of 3-furylfulgides: impact of size and bond flexibility of the nonaromatic alkylidene group. Acta Cryst. 2015;B71:535–42.10.1107/S2052520615015267Search in Google Scholar PubMed

13. Harada J, Nakajima R, Ogawa K. X-ray diffraction analysis of photochromic reaction of fulgides: crystalline state reaction induced by two-photon excitation. J Am Chem Soc. 2008;130:7085–91.10.1021/ja800353uSearch in Google Scholar PubMed

14. Asiri AM, Heller HG, Hursthouse MB, Karalulov A. Tribochromic compounds, exemplified by 3-dicyclopropylmethylene-5-dicyanomethylene-4-diphenylmethylenetetrahydrofuran-2-one. Chem Commun. 2000;799–800.10.1039/b001567iSearch in Google Scholar

15. Asiri AMA, Heller HG, Hughes DS, Hursthouse MB, Kendrick J, Leusen FJJ, et al. A mechanophysical phase transition provides a dramatic example of colour polymorphism: the tribochromism of a substituted tri(methylene) tetrahydrofuran-2-one. Chem Cent J. 2014;8:70.10.1186/s13065-014-0070-3Search in Google Scholar PubMed PubMed Central

16. Asiri AMA, Cleeves A, Heller HG. Studies on piezochromic photochromic (E)-5-dicyanomethylene-3-[1-(2,5-dimethyl-3-furyl)ethylidene]-4-diphenylmethylenetetrahydrofuran-2-one and related photochromic compounds. J Chem Soc Perkin Trans.I 2000;1:2741–4.10.1039/b002414gSearch in Google Scholar

17. Towns A. Photochromic Dyes. Phys. Sci. Rev. DOI: 10.1515/psr-2020-0191.10.1515/psr-2020-0191Search in Google Scholar

18. Stobbe H. II. Condensation des Acetophenons mit Bernsteinsäureester. Justus Liebigs Ann Chem. 1899;308:114–55.10.1002/jlac.18993080107Search in Google Scholar

19. Extrasynthese, (E)-Aberchrome 540 / 8200. www.extrasynthese.com/organics/12-e-aberchrome-540.html.Search in Google Scholar

20. TCI America. Aberchrome 670 94856-25-4. www.tcichemicals.com/US/en/p/A2869.Search in Google Scholar

21. International Union of Pure and Applied Chemistry Organic Chemistry Division Commission on Photochemistry. Chemical actinometry (IUPAC Technical Report). Pure Appl Chem. 2004;76:2105–46.10.1351/pac200476122105Search in Google Scholar

22. Goldschmidt S, Riedle R, Reichardt A. Über die Bisdiphenylenfulgide und die Spaltung der Bisdiphenylenefulgensäure in optisch active Komponenten. Justus Liebigs Ann Chem. 1957;604:121–32.10.1002/jlac.19576040117Search in Google Scholar

23. Hart RJ, Heller HG, Salisbury K. The photochemical rearrangements of some photochromic fulgimides. Chem Commun. 1968;1627–8.10.1039/c19680001627Search in Google Scholar

24. Heller HG, Koh K, Elliot C, Whittall J. Fulgides and fulgimides for practical applications. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst. 1994;246:79–86.10.1080/10587259408037792Search in Google Scholar

25. Xiao J-P, Han Y, Chen Y, Li W, Fan M-G. Studies on synthesis and photochromism of a novel class of fulgimide: (Z)-4-Oxazolylfulgimide. Chin J Chem. 2004;22:100–2.10.1002/cjoc.20040220121Search in Google Scholar

26. Badland M, Cleeves A, Heller HG, Hughes DS, Hursthouse MB. Photochromic heteroaromatic thiofulgides and dimethoxybutanoic acid lactones. Chem Commun. 2000;1567–8.10.1039/b002033hSearch in Google Scholar

27. Heller HG, Koh K, Kose M, Rowles N. The design and development of new thermally stable infra-red active photochromic compounds. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst. 1997;297:73–80.10.1080/10587259708036105Search in Google Scholar

28. Kose M, Orhan E, Büyükgüngör O. Synthesis of novel photochromic methyl cyanoacetate-condensed fulgide derivatives. J Photochem Photobiol A: Chem. 2007;188:358–63.10.1016/j.jphotochem.2006.12.036Search in Google Scholar

29. Heller HG, Hughes DS, Hursthouse MB, Rowles NG. Thermally stable fatigue resistant near infrared active photochromic compounds, exemplified by 6-amino-7-cyano-3-(dicyclopropylmethylene)-4-(2,5-dimethyl-3-furyl)-benzofuran-2(3H)-one. Chem Commun. 2000;1397–8.10.1039/b003496gSearch in Google Scholar

30. Margerum JD, Miller LJ. In: Brown GH, editor. Photochromism. New York: John Wiley & Sons, 1971 Chapter 6 (“Photochromic Processes by Tautomerism”):557–632.Search in Google Scholar

31. Matsushima R, Sakaguchi H. Comparison of the photochromic properties of fulgides and fulgimides. J Photochem Photobiol A: Chem. 1997;108:239–45.10.1016/S1010-6030(97)00095-6Search in Google Scholar

32. Yokoyama Y, Inoue T, Yokoyama M, Goto T, Iwai T, Kera N, et al. Effects of steric bulkiness of substituents on quantum yields of photochromic reactions of furylfulgides. Bull Chem Soc Jpn. 1994;67:3297–303.10.1246/bcsj.67.3297Search in Google Scholar

33. Yokoyama Y, Goto T, Inoue T, Yokoyama M, Kurita Y. Fulgides as efficient photochromic compounds. Role of the substituent on furylalkylidene moiety of furylfulgides in the photoreaction. Chem Lett. 1988;17:1049–52.10.1246/cl.1988.1049Search in Google Scholar

34. Kiji J, Okano T, Kitamura H, Yokoyama Y, Kubota S, Kurita Y. Synthesis and photochromic properties of fulgides with a t-butyl substituent on the furyl- or thienylmethylidene moiety. Bull Chem Soc Jpn. 1995;68:616–9.10.1246/bcsj.68.616Search in Google Scholar

35. Yokoyama Y, Iwai T, Kera N, Hitomi I, Kurita Y. Steric effect of alkylidene groups of furylfulgides on the photochromic behavior. Chem Lett. 1990;263–4.10.1246/cl.1990.263Search in Google Scholar

36. Santiago A, Becker RS. Photochromic fulgides. Spectroscopy and mechanism of photoreactions. J Am Chem Soc. 1968;90:3654–8.10.1021/ja01016a009Search in Google Scholar

37. Darcy PJ, Heller HG, Strydom PJ, Whittall J. Photochromic heterocyclic fulgides. Part 2. Electrocyclic reactions of (E)-α-2,5-Dimethyl-3-furylethylidene(alkyl-substituted methylene)-succinic anhydrides. J Chem Soc Perkin Trans I. 1981;202–5.10.1039/P19810000202Search in Google Scholar

38. Glaze AP, Heller HG, Whittall J. Photochromic heterocyclic fulgides. Part 7. (E)-Adamantylidene-[1-(2,5-dimethyl-3-furyl)ethylidene]succinic anhydride and derivatives: model photochromic compounds for optical recording media. J Chem Soc Perkin Trans 2. 1992;2:591–4.10.1039/p29920000591Search in Google Scholar

39. Stobbe H, Eckert R. Eine Parallele farbiger Furyl- und Phenyl-Fulgide. (11. Abhandlung über Butadiënverbindungen). Chem Ber. 1905;38:4075–81.10.1002/cber.19050380479Search in Google Scholar

40. Heller HG, Oliver S. Photochromic Heterocyclic Fulgides. Part 1. Rearrangement reactions of (E)-α-3-Furylethylidene(isopropylidene)succinic anhydride. J Chem Soc Perkin Trans I. 1981;197–201.10.1039/P19810000197Search in Google Scholar

41. Yokoyama Y, Takahashi K. Trifluoromethyl-substituted photochromic Indolylfulgide. A remarkably durable fulgide towards photochemical and thermal treatments. Chem Lett. 1996;1037–8.10.1246/cl.1996.1037Search in Google Scholar

42. Reinfelds M, Hermanns V, Halbritter T, Wachtveitl J, Braun M, Slanina T, et al. Broadly absorbing fulgide derivative as a universal chemical actinometer for the UV to NIR region. ChemPhotoChem. 2019;3:441–9.10.1002/cptc.201900010Search in Google Scholar

43. Heller HG, Oliver SN, Whittal J, Johncock W, Darcy PJ, Trundle C. (The Plessey Co plc). Photochromic compounds and their use in photoreactive lenses. UK Patent GB2146327B. 1986.Search in Google Scholar

44. Yokoyama Y, Nakata H, Sugama K, Yokoyama Y. Photochromism and kinetics of heliochromic Benzothienylfulgides. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst. 2000;344:253–8.10.1080/10587250008023845Search in Google Scholar

45. Heller HG. Encyclopedia of materials: science and technology, 2nd ed. Elsevier, 2001 (“Photochromic Materials (Organic)”):6904–9.10.1016/B0-08-043152-6/01224-9Search in Google Scholar

46. Heller HG, Oliver SN, Whittal J, Tomlinson I. (The Plessey Co plc). Photochromic spiropyran compounds. UK Patent GB2190379B. 1990.Search in Google Scholar

47. Sothman B. Making the mold and breaking the mold (The rise and fall and rise of SOLA Optical). http://www.solahistory.com/ Search in Google Scholar

48. Kobayakawa T. Photochromism of spiro-oxazines. In: Third International Symposium on Photochromism, Fukuoka, 1999.Search in Google Scholar

49. Towns A. Spirooxazine dyes. Phys Sci Rev. 2020;5. DOI:doi.org/10.1515/psr-2020-0013.Search in Google Scholar

50. Imura T, Kida Y, Tanaka T. (Tokuyama Soda KK). Fulgimide compounds and production thereof. Japanese Patent JPS6438063(A). 1989.Search in Google Scholar

51. Imura S, Tanizawa T, Kobayakawa T. (Tokuyama Corp.). Cyclopropyl-substituted spiro-photochromic compounds. European Patent Application EP0629626A2. 1994.Search in Google Scholar

52. Kawabata Y, Momoda J, Nagoh H. (Tokuyama Corp.). Photochromic composition. European Patent Application EP0965628A1. 2000.Search in Google Scholar

53. Mann C, Melzig M, Weigand U. (Optische Werke G. Rodenstock). World Patent Application WO 02/22594. 2002.Search in Google Scholar

54. Towns A. Naphthopyran dyes. Phys Sci Rev. 2020;5. DOI:doi/10.1515/psr-2019-0085.Search in Google Scholar

55. Kohno Y, Tamura Y, Matsushima R. Simple full-color rewritable film with photochromic fulgide derivatives. J Photochem Photobiol A: Chem. 2009;201:98–101.10.1016/j.jphotochem.2008.10.006Search in Google Scholar

56. Yao B, Wang Y, Menke N, Lei M, Zheng Y, Ren L, et al. Optical properties and applications of photochromic fulgides. Mol Cryst Liq Cryst. 2005;430:211–9.10.1080/15421400590946415Search in Google Scholar

57. Zong Z, Menke N, Yao B, Wang Y, Chen Y. Polarization multiplexing, angle multiplexing and circumrotation multiplexing holographic recording experiments with 3-indolylbenzylfulgimide/PMMA film. Appl Mech Mater. 2012;130-134:2035–41.10.4028/www.scientific.net/AMM.130-134.2035Search in Google Scholar

58. Chao L, Menke N, Yao B, Lei M, Wang Y, Sun X, et al. Optical storage properties of different fulgides. Adv Mater Res. 2013;660:24–9.10.4028/www.scientific.net/AMR.660.24Search in Google Scholar

59. Menke N, Yao B, Wang Y, Dong W, Lei M, Chen Y, et al. Spectral relationship of photoinduced refractive index and absorption changes in fulgide films. J Mod Opt. 2008;55:1003–11.10.1080/09500340701552289Search in Google Scholar

60. Rybalkin VP, Pluzhnikov SY, Popova LL, Revinskii YV, Tikhomirova KS, Komissarova OA, et al. A novel approach to fluorescent photochromic fulgides. Mendeleev Commun. 2016;26:21–3.10.1016/j.mencom.2016.01.009Search in Google Scholar

61. Jiao Y, Yang R, Luo Y, Liu L, Xu B, Tian W. Fulgide derivative based solid-state reversible fluorescent switch for advanced optical memory. CCS Chem. 2021;3. DOI:doi.org/10.31635/ccschem.021.202000673.Search in Google Scholar

62. Weerasekara RK, Uekusa H, Hettiarachchi CV. Multicolor photochromism of fulgide mixed crystals with enhanced fatigue resistance. Cryst Growth Des. 2017;17:3040–7.10.1021/acs.cgd.6b01708Search in Google Scholar