Jump to ContentJump to Main Navigation
Show Summary Details
In This Section

Organic Photonics and Photovoltaics

Editor-in-Chief: Facchetti, Antonio

Ed. by Ponomarenko, Sergei

1 Issue per year


Emerging Science

Open Access
Online
ISSN
2299-3177
See all formats and pricing
In This Section

Spiropyran salts and their neutral precursors: synthesis, crystal structure, photochromic transformations in solutions and solid state

E.A. Yurieva
    / S.M. Aldoshin
      Published Online: 2015-06-16 | DOI: https://doi.org/10.1515/oph-2015-0004

      Abstract

      This review covers investigations of spiropyran iodides with N-substituted indoline fragment, and with the pyran cycle being annelated to N-methylated pyridine ring. The schemes of synthesis of iodides and their neutral precursors, as well as results of X-ray analysis and photochemical study of the crystals of the obtained compounds are presented. Based on our and literature data, the relationship between the structure and photochromic properties has been discussed for a series of salts and neutral pyridospiropyrans.

      Keywords: Photochromic spiropyrans; Crystalline structure; Solid state photochromic transformations; Correlation between the structure and properties

      References

      • [1] R. Guglielmetti, Chapter 8, In: H. Durr, H. Bouas-Laurent (Eds.), Photochromism: Molecules and Systems, Elsevier, Amsterdam, 1990.

      • [2] S.M. Aldoshin, Chapter 7, In: J.C. Crano, R.J. Guglimetti (Eds.), Organic Photochromic and Thermochromic Compounds, Kluwer Academic, Plenum Publishers, New York, 1999.

      • [3] S.V. Paramonov, V. Lokshin, O.A. Fedorova, Spiropyran, chromene or spirooxazine ligands: Insights into mutual relations between complexing and photochromic properties, J. Photochem. Photobiol. C: Photochem. Rev., 12, 2011, 209. [Web of Science] [Crossref]

      • [4] R. Klajn, Spiropyran-based dynamicmaterials, Chem. Soc. Rev., 43, 2014, 148. [Crossref]

      • [5] H.J. Suh,W.T. Lim, J.Z. Cui, H.S. Lee, G.H. Kim, N.H. Heo and S.H. Kim, The crystalline-state photochromism, thermochromism and X-ray structural characterization of a new spiroxazine, Dyes Pigm. 57, 2002, 149.

      • [6] D.G. Patel, J.B. Benedict, R.A. Kopelman and N.L. Frank, Photochromism of a spirooxazine in the single crystalline phase, Chem. Commun., 2005, 2208. [Crossref]

      • [7] S. Bénard and P. Yu, New Spiropyrans Showing Crystalline-State Photochromism, Adv. Mater. 12, 2000, 48.

      • [8] S. Bénard and P. Yu, A spirooxazine showing crystalline state photochromism, Chem. Commun., 2000, 65. [Crossref]

      • [9] S. Bénard, E. Rivière, P. Yu, K. Nakatani and J. F. Delouis, A Photochromic Molecule-BasedMagnet, Chem.Mater. 13, 2001, 159. [Crossref]

      • [10] A. Léaustic, A. Dupont, P. Yu and R. Clément, Photochromism of cationic spiropyran-doped silica gels, New J. Chem. 25, 2001, 1297.

      • [11] S. Bénard, A. Léaustic, E. Rivière, P. Yu and R. Clément, Interplay between Magnetism and Photochromism in Spiropyran-MnPS3 Intercalation Compounds, Chem. Mater. 13, 2001, 3709. [Crossref]

      • [12] I. Kashima, M. Okubo, Y. Ono, M. Itoi, N. Kida, M. Hikita, M. Enomoto and N. Kojima, Ferromagnetism and its photo-induced effect in 2D iron mixed-valence complex coupled with photochromic spiropyran, Synth. Met. 155, 2005, 703.

      • [13] S.M. Aldoshin, N.A. Sanina, V.I. Minkin, N.A. Voloshin, V.N. Ikorskii, V.I. Ovcharenko, V.A. Smirnov and N.K. Nagaeva, Molecular photochromic ferromagnetic based on the layered polymeric tris-oxalate of Cr(III), Mn(II) and 1-

      • [(1’,3’,3’-trimethyl- 6-nitrospiro

      • [2H-1-benzopyran-2,2’-indoline]-8-yl)methyl] pyridinium, J. Mol. Struct. 826, 2007, 69.

      • [14] S.M. Aldoshin, N.A. Sanina, V.A. Nadtochenko, E.A. Yurieva, V.I. Minkin, N.A. Voloshin, V.N. Ikorskii and V.I. Ovcharenko, Specific spectral properties of a photochromic ferromagnetic (C25H23N3O3Cl)CrMn(C2O4)3·H2O, Russ. Chem. Bull. Int. Ed. 56, 2007, 1095. (Eng. Transl.)

      • [15] S.M. Aldoshin, Heading to photoswitchable magnets, J. Photochem. Photobiol. A: Chem. 200, 2008, 19.

      • [16] E.A. Yurieva, S.M. Aldoshin, L.A. Nikonova, G.V. Shilov and V.A. Nadtochenko,

      • [1-Benzyl-3,3,5′,6′-tetramethylspiro

      • [indoline- 2,2′-

      • [2H]pyrano

      • [3,2-b]-pyridinium] iodide, its hydrate, and a neutral precursor of the salts: synthesis, crystal structure, photochromic transformations in solutions and in crystals, Russ. Chem. Bull. Int. Ed. 60, 2011, 1401. (Eng. Transl.) [Web of Science]

      • [17] S.M. Aldoshin, L.A. Nikonova, V.A. Smirnov, G.V. Shilov and N.K. Nagaeva, Structure and photochromic properties of a singlecrystalline spiro

      • [indolinepyranopyridinium] salt, Russ. Chem. Bull. Int. Ed. 54, 2005, 2113. (Eng. Transl.)

      • [18] S.M. Aldoshin, L.A. Nikonova, V.A. Smirnov, G.V. Shilov and N.K. Nagaeva, Structure and photochromic properties of single crystals of spiropyran salts, J. Mol. Struct. 750, 2005, 158.

      • [19] S.M. Aldoshin, Cations of Photochromic Spiropyrans as Promising Blocks for Polyfunctional Materials, Mol. Cryst. Liq. Cryst. 430, 2005, 157.

      • [20] S.M. Aldoshin, L.A. Nikonova, G.V. Shilov, E.A. Bikanina, N.K. Artemova and V.A. Smirnov, The influence of an N-substituent in the indoline fragment of pyrano-pyridine spiropyran salts on their crystalline structure and photochromic properties, J. Mol. Structure 794, 2006, 103.

      • [21] V.V. Tkachev, S.M. Aldoshin, N.A. Sanina, B.S. Luk’yanov, V.I. Minkin, A.N. Utenyshev, K.N. Khalanskii and Yu. S. Alekseenko, Photo-and thermochromic spiranes. 29. New photochromic indolinospiropyrans containing a quinoline fragment, Chem. Heterocycl. Compounds Int. Ed. 43, 2007, 576. (Eng. Transl.)

      • [22] F.H. Allen,O. Kennard, D.G.Watson, L. Brammer, A.G. Orpen and R. Taylor, Tables of Bond Lengths determined by X-Ray and Neutron Diffraction. Part I. Bond Lengths in Organic Compounds, J. Chem. Soc. perkin trans. II, 1987, S1-S19.

      • [23] P. Naumov, P. Yu and K. Sakurai, Electronic Tera-Order Stabilization of Photoinduced Metastable Species: Structure of the Photochromic Product of Spiropyran Determined with in situ Single Crystal X-ray Photodiffraction, J. Phys. Chem. A 112, 2008, 5810. [Web of Science]

      About the article

      Received: 2014-10-27

      Accepted: 2015-03-09

      Published Online: 2015-06-16



      Citation Information: Organic Photonics and Photovoltaics, ISSN (Online) 2299-3177, DOI: https://doi.org/10.1515/oph-2015-0004. Export Citation

      ©2015 E.A. Yurieva, S.M. Aldoshin. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. (CC BY-NC-ND 3.0)

      Comments (0)

      Please log in or register to comment.
      Log in