Skip to main content

Photo-Switching of Circularly Polarized Luminescence

  • Chapter
  • First Online:
Circularly Polarized Luminescence of Isolated Small Organic Molecules

Abstract

Circularly polarized luminescence (CPL) emission from chiral molecular systems is readily switched by means of external stimuli such as temperature, solvent, chemicals, and light irradiation. Since CPL is one of the emission phenomena, it can be modulated in a similar manner to the emission switching. The ON-OFF switching of emission intensity of chiral molecular systems may simply lead to the modulation of CPL intensity. Apart from the modulation of emission intensity, the chiral structures including chiral arrangement of fluorophores or metal coordination geometries are switched by external stimuli, changing the dissymmetry factors, i.e., the quality of CPL. In this chapter, we review the design of chiroptical photo-switches based on photochromic molecules that modulate the CPL property in response to photo-irradiation in a dynamic manner.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Maeda H, Bando Y, Shimomura K, Yamada I, Naito M, Nobusawa K, Tsumatori H, Kawai T (2011) Chemical-stimuli-controllable circularly polarized luminescence from anion-responsive π-conjugated molecules. J Am Chem Soc 133:9266–9269

    Article  CAS  PubMed  Google Scholar 

  2. Saleh N, Moore B, Srebro M, Vanthuyne N, Toupet L, Williams JA, Roussel C, Deol KK, Muller G, Autschbach J, Crassous J (2015) Acid/base-triggered switching of circularly polarized luminescence and electronic circular dichroism in organic and organometallic helicenes. Chem Eur J 21:1673–1681

    Article  CAS  PubMed  Google Scholar 

  3. Amako T, Nakabayashi K, Mori T, Inoue Y, Fujiki M, Imai Y (2014) Sign inversion of circularly polarized luminescence by geometry manipulation of four naphthalene units introduced into a tartaric acid scaffold. Chem Commun 50:12836–12839

    Article  CAS  Google Scholar 

  4. Kumar J, Nakashima T, Tsumatori H, Kawai T (2014) Circularly polarized luminescence in chiral aggregates: dependence of morphology on luminescence dissymmetry. J Phys Chem Lett 5:316–321

    Article  PubMed  CAS  Google Scholar 

  5. Kumar J, Tsumatori H, Yuasa J, Kawai T, Nakashima T (2015) Self-discriminating termination of chiral supramolecular polymerization: tuning the length of nanofibers. Angew Chem Int Ed 54:5943–5947

    Article  CAS  Google Scholar 

  6. Sethy R, Kumar J, Métivier R, Louis M, Nakatani K, Mecheri NMT, Subhakumari A, Thomas KG, Kawai T, Nakashima T (2017) Enantioselective light harvesting with perylenediimide guests on self-assembled chiral naphthalenediimide nanofibers. Angew Chem Int Ed 56:15053–15057

    Article  CAS  Google Scholar 

  7. Kumar J, Kawai T, Nakashima T (2017) Circularly polarized luminescence in chiral silver nanoclusters. Chem Commun 53:1269–1272

    Article  CAS  Google Scholar 

  8. Morisue M, Yumura T, Sawada R, Naito M, Kuroda Y, Chujo Y (2016) Oligoamylose-entwined porphyrin: excited-state induced-fit for chirality induction. Chem Commun 52:2481–2484

    Article  CAS  Google Scholar 

  9. Yuasa J, Ueno H, Kawai T (2014) Sign reversal of a large circularly polarized luminescence signal by the twisting motion of a bidentate ligand. Chem Eur J 20:8621–8627

    Article  CAS  PubMed  Google Scholar 

  10. Imai Y, Nakano Y, Kawai T, Yuasa J (2018) A smart sensing method for object identification using circularly polarized luminescence from coordination-driven self-assembly. Angew Chem Int Ed 57:8973–8978

    Article  CAS  Google Scholar 

  11. Nagata Y, Nishikawa T, Suginome M (2014) Chirality-switchable circularly polarized luminescence in solution based on the solvent-dependent helix inversion of poly(quinoxaline-2,3-diyl)s. Chem Commun 50:9951–9953

    Article  CAS  Google Scholar 

  12. Zhang YJ, Oka T, Suzuki R, Ye JT, Iwasa Y (2014) Electrically switchable chiral light-emitting transistor. Science 344:725–728

    Article  CAS  PubMed  Google Scholar 

  13. Nishizawa N, Nishibayashi K, Munekata H (2017) Pure circular polarization electroluminescence at room temperature with spin-polarized light-emitting diodes. Proc Natl Acad Sci U S A 114:1783–1788

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Sherson JF, Krauter H, Olsson RK, Julsgaard B, Hammerer K, Cirac I, Polzik ES (2006) Quantum teleportation between light and matter. Nature 443:557–560

    Article  CAS  PubMed  Google Scholar 

  15. Feringa BL, van Delden RA, Koumura N, Geertsema EM (2000) Chiroptical molecular switches. Chem Rev 100:1789–1816

    Article  CAS  PubMed  Google Scholar 

  16. Yildiz I, Deniz E, Raymo FM (2009) Fluorescence modulation with photochromic switches in nanostructured constructs. Chem Soc Rev 38:1859–1867

    Article  CAS  PubMed  Google Scholar 

  17. Irie M, Fukaminato T, Matsuda K, Kobatake S (2014) Photochromism of diarylethene molecules and crystals: memories, switches, and actuators. Chem Rev 114:12174–12277

    Article  CAS  PubMed  Google Scholar 

  18. Fukaminato T (2011) Single-molecule fluorescence photoswitching: design and synthesis of photoswitchable fluorescent molecules. J Photochem Photobiol C 12:177–208

    Article  CAS  Google Scholar 

  19. Saika T, Iyoda T, Honda K, Shimidzu T (1992) Emission control of a pyrene-thioindigo compound. J Chem Soc Chem Commun 1992:591–592

    Article  Google Scholar 

  20. Wang J, Kulago A, Browne WR, Feringa BL (2010) Photoswitchable intramolecular H-stacking of perylenebisimide. J Am Chem Soc 132:4191–4192

    Article  CAS  PubMed  Google Scholar 

  21. Heller HG, Oliver S (1981) Photochromic heterocyclic fulgides. 1. Rearrangement reactions of (E)-alpha-3-furylethylidene(isopropylidene)succinic anhydride. J Chem Soc Perkin Trans 1:197–202

    Article  Google Scholar 

  22. Hayasaka H, Miyashita T, Tamura K, Akagi K (2010) Helically π-stacked conjugated polymers bearing photoresponsive and chiral moieties in side chains: reversible photoisomerization-enforced switching between emission and quenching of circularly polarized fluorescence. Adv Funct Mater 20:1243–1250

    Article  CAS  Google Scholar 

  23. Berova N, Nakanishi K, Woody RW (2000) Circular dichroism: principal and applications, 2nd edn. Wiley-VCH, New York

    Google Scholar 

  24. Peeters M, Christiaans MPT, Janssen RAJ, Schoo HFM, Dekkers HPJM, Meijer EW (1997) Circularly polarized electroluminescence from a polymer light-emitting diode. J Am Chem Soc 119:9909–9910

    Article  CAS  Google Scholar 

  25. Geng Y, Trajkovska A, Katsis D, Ou JJ, Culligan SW, Chen SH (2002) Synthesis, characterization, and optical properties of monodisperse chiral oligofluorenes. J Am Chem Soc 124:8337–8347

    Article  CAS  PubMed  Google Scholar 

  26. Wilson JN, Steffen W, McKenzie TG, Lieser G, Oda M, Neher D, Bunz UHF (2002) Chiroptical properties of poly(p-phenyleneethynylene) copolymers in thin films: large g-values. J Am Chem Soc 124:6830–6831

    Article  CAS  PubMed  Google Scholar 

  27. Satrijo A, Meskers SCJ, Swager TM (2006) Probing a conjugated polymer’s transfer on organization-dependent properties from solutions to films. J Am Chem Soc 128:9030–9031

    Article  CAS  PubMed  Google Scholar 

  28. Berova N, Di Bari L, Pescitelli G (2007) Application of electronic circular dichroism in configuration and conformational analysis of organic compounds. Chem Soc Rev 36:914–931

    Article  CAS  PubMed  Google Scholar 

  29. Nakashima T, Atsumi K, Kawai S, Nakagawa T, Hasegawa Y, Kawai T (2007) Photochromism of thiazole-containing triangle terarylenes. Eur J Org Chem 2007:3212–3218

    Article  CAS  Google Scholar 

  30. Fukumoto S, Nakashima T, Kawai T (2011) Photon-quantitative reaction of a dithiazolylarylene in solution. Angew Chem Int Ed 50:1565–1568

    Article  CAS  Google Scholar 

  31. Fukumoto S, Nakashima T, Kawai T (2011) Intramolecular hydrogen bonding in a triangular dithiazolyl-azaindole for efficient photoreactivity in polar and nonpolar solvents. Eur J Org Chem 2011:5047–5053

    Article  CAS  Google Scholar 

  32. Li R, Nakashima T, Galangau O, Iijima S, Kanazawa R, Kawai T (2015) Photon-quantitative 6p-electrocyclization of a diarylbenzo[b]thiophene in polar medium. Chem Asian J 10:1725–1730

    Article  CAS  PubMed  Google Scholar 

  33. Nakagawa T, Miyasaka Y, Yokoyama Y (2018) Photochromism of a spiro-functionalized diarylethene derivative: multi-colour fluorescence modulation with a photon-quantitative photocyclization reactivity. Chem Commun 54:3207–3210

    Article  CAS  Google Scholar 

  34. Gavrel G, Yu P, Léaustic A, Gillot R, Métivier R, Nakatani K (2012) 4,4′-Bithiazole-based tetraarylenes: new photochromes with unique photoreactive patterns. Chem Commun 48:10111–10113

    Article  CAS  Google Scholar 

  35. Nakashima T, Yamamoto K, Kimura Y, Kawai T (2013) Chiral photoresponsive tetrathiazoles that provide snapshots of folding states. Chem Eur J 19:16972–16980

    Article  CAS  PubMed  Google Scholar 

  36. Nakashima T, Imamura K, Yamamoto K, Kimura Y, Katao S, Hashimoto Y, Kawai T (2014) Synthesis, structure, and properties of α,β-linked oligothiazoles with controlled sequence. Chem Eur J 20:13722–13729

    Article  CAS  PubMed  Google Scholar 

  37. Hashimoto Y, Nakashima T, Shimizu D, Kawai T (2016) Photoswitching of an intramolecular chiral stack in a helical tetrathiazole. Chem Commun 52:5171–5174

    Article  CAS  Google Scholar 

  38. Sanchez-Cárnerero EM, Agarrabeitia AR, Moreno F, Maroto BL, Muller G, Ortiz MJ, de la Moya S (2015) Circularly polarized luminescence from simple organic molecules. Chem Eur J 21:13488–13500

    Article  PubMed  CAS  Google Scholar 

  39. Brittain H, Ambrozich DL, Saburi M, Fendler JH (1980) Enhanced optical activity associated with chiral 1-(1-hydroxyhexyl)pyrene excimer formation. J Am Chem Soc 102:6372–6374

    Article  CAS  Google Scholar 

  40. Kano K, Matsumoto H, Hashimoto S, Sisido M, Imanishi Y (1985) Chiral pyrene excimer in the γ-cyclodextrin cavity. J Am Chem Soc 107:6117–6118

    Article  CAS  Google Scholar 

  41. Richardson FS, Riehl JP (1977) Circularly polarized luminescence spectroscopy. Chem Rev 77:773–792

    Article  CAS  Google Scholar 

  42. Lunkley JL, Shirotani D, Yamanari K, Kaizaki S, Muller G (2008) Extraordinary circularly polarized luminescence activity exhibited by cesium tetrakis(3-heptafluoro-butylryl-(+)-camphorato) Eu(III) complexes in EtOH and CHCl3 solutions. J Am Chem Soc 130:13814–13815

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  43. Carr R, Evans NH, Parker D (2012) Lanthanide complexes as chiral probes exploiting circularly polarized luminescence. Chem Soc Rev 41:7673–7686

    Article  CAS  PubMed  Google Scholar 

  44. Aspinall HC (2002) Chiral lanthanide complexes: coordination chemistry and applications. Chem Rev 102:1807–1850

    Article  CAS  PubMed  Google Scholar 

  45. Bing TY, Kawai T, Yuasa J (2018) Ligand-to-ligand interactions that direct formation of D2-symmetrical alternating circular helicate. J Am Chem Soc 140:3683–3689

    Article  CAS  PubMed  Google Scholar 

  46. Hasegawa Y, Nakagawa T, Kawai T (2010) Recent progress of luminescent metal complexes with photochromic units. Coord Chem Rev 254:2643–2651

    Article  CAS  Google Scholar 

  47. Cheng HB, Hu GF, Zhang ZH, Gao L, Gao X, Wu HC (2016) Photocontrolled reversible luminescent lanthanide molecular switch based on a diarylethene-europium dyad. Inorg Chem 55:7962–7968

    Article  CAS  PubMed  Google Scholar 

  48. He X, Norel L, Hervault YM, Métivier R, D’Aleo A, Maury O, Rigaut S (2016) Modulation of Eu(III) and Yb(III) luminescence using a DTE photochromic ligand. Inorg Chem 55:12635–12643

    Article  CAS  PubMed  Google Scholar 

  49. Hashimoto Y, Nakashima T, Yamada M, Yuasa J, Rapenne G, Kawai T (2018) Hierarchical emergence and dynamic control of chirality in a photoresponsive dinuclear complex. J Phys Chem Lett 9:2151–2157

    Article  CAS  PubMed  Google Scholar 

  50. Metcalf DH, Snyder SW, Demas JN, Richardson FS (1990) Chiral dynamics in the excited state of a stereochemically labile metal complex. J Phys Chem 94:7143–7153

    Article  CAS  Google Scholar 

  51. Liu M, Zhang L, Wang T (2015) Supramolecular chirality in self-assembled systems. Chem Rev 115:7304–7397

    Article  CAS  PubMed  Google Scholar 

  52. Kumar J, Nakashima T, Kawai T (2015) Circularly polarized luminescence in chiral molecules and supramolecular assemblies. J Phys Chem Lett 6:3445–3452

    Article  CAS  PubMed  Google Scholar 

  53. Gopal A, Hifsudheen M, Furumi S, Takeuchi M, Ajayaghosh A (2012) Thermally assisted photonic inversion of supramolecular handedness. Angew Chem Int Ed 51:10505–10509

    Article  CAS  Google Scholar 

  54. Miao W, Wang S, Liu M (2017) Reversible quadruple switching with optical, chiroptical, helicity, and macropattern in self-assembled spiropyran gels. Adv Funct Mater 27:1701368

    Article  CAS  Google Scholar 

  55. Jiang H, Jiang Y, Han J, Zhang L, Liu M (2018) Helical nanostructures: chirality transfer and a photodriven transformation from superhelix to nanokebab. Angew Chem Int Ed 58:785–790

    Article  CAS  Google Scholar 

  56. Hashimoto Y, Nakashima T, Kuno J, Yamada M, Kawai T (2018) Dynamic modulation of circularly polarized luminescence in photoresponsive assemblies. ChemNanoMat 4:815–820

    Article  CAS  Google Scholar 

  57. Bu J, Watanabe K, Hayasaka H, Akagi K (2014) Photochemically colour-tuneable white fluorescence illuminants consisting of conjugated polymer nanospheres. Nat Commun 5:3799-1–3799-8

    Article  CAS  Google Scholar 

  58. Su J, Fukaminato T, Placial JP, Onodera T, Suzuki R, Oikawa H, Brosseau A, Brisset F, Pansu R, Nakatani K, Métivier R (2015) Giant amplification of photoswitching by a few photons in fluorescent photochromic organic nanoparticles. Angew Chem Int Ed 55:3662–3666

    Article  CAS  Google Scholar 

  59. Chen SH, Katsis D, Schmid AW, Mastrangelo JC, Tsutsui T, Blanton TN (1999) Circularly polarized light generated by photoexcitation of luminophores in glassy liquid-crystal films. Nature 397:506–508

    Article  CAS  Google Scholar 

  60. San Jose BA, Yan J, Akagi K (2014) Dynamic switching of the circularly polarized luminescence of disubstituted polyacetylene by selective transmission through a thermotropic chiral nematic liquid crystal. Angew Chem Int Ed 53:10641–10644

    Article  CAS  Google Scholar 

  61. Vicario J, Katsonis N, Ramon BS, Bastiaansen CWM, Broer DJ, Feringa BL (1999) Nanomotor rotates microscale objects. Nature 440:163

    Google Scholar 

  62. Hayasaka H, Miyashita T, Nakayama M, Kuwada K, Akagi K (2012) Dynamic photoswitching of helical inversion in liquid crystals containing photoresponsive axially chiral dopants. J Am Chem Soc 134:3758–3765

    Article  CAS  PubMed  Google Scholar 

  63. Li Y, Urbas A, Li Q (2012) Reversible light-directed red, green, and blue reflection with thermal stability enabled by a self-organized helical superstructure. J Am Chem Soc 134:9573–9576

    Article  CAS  PubMed  Google Scholar 

  64. Zheng ZG, Li Y, Bisoyi HK, Wang L, Bunning TJ, Li Q (2016) Three-dimensional control of the helical axis of a chiral nematic liquid crystal by light. Nature 531:352–356

    Article  CAS  PubMed  Google Scholar 

  65. Brandt JR, Salerno F, Fuchter MJ (2017) The added value of small-molecule chirality in technological applications. Nat Rev Chem 1:0045-1–0045-12

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Takuya Nakashima or Tsuyoshi Kawai .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2020 Springer Nature Singapore Pte Ltd.

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Nakashima, T., Kawai, T. (2020). Photo-Switching of Circularly Polarized Luminescence. In: Mori, T. (eds) Circularly Polarized Luminescence of Isolated Small Organic Molecules. Springer, Singapore. https://doi.org/10.1007/978-981-15-2309-0_8

Download citation

Publish with us

Policies and ethics