Skip to main content

Mechanical-Stimulation-Triggered and Solvent-Vapor-Induced Reverse Single-Crystal-to-Single-Crystal Phase Transitions with Alterations of the Luminescence Color

  • Chapter
  • First Online:

Part of the book series: Springer Theses ((Springer Theses))

Abstract

Herein, the first example of reversible change of the luminescence based on two SCSC phase transitions via mechanical cutting and solvent-vapor adsorption is described. Crystallization of a gold(I) complex that bears CF3 and biaryl moieties from CH2Cl2/MeOH afforded a green-emitting single crystal packed in a polar space group (Pna21). The green-emitting single crystals included MeOH molecules. Upon cutting the crystal under MeOH vapor at 22 °C, the green-emitting single crystal spontaneously changed into a centrosymmetric orange-emitting single crystal (\(P\bar{1}\)) under concomitant release of MeOH. Remarkably, the initial green-emitting crystal could be recovered from the orange-emitting crystal by a solvent-induced SCSC transition under saturated MeOH vapor. The combination of two different types of SCSC phase transitions enables the reversible structural and photoluminescent alternations.

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

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   109.99
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

Learn about institutional subscriptions

References

  1. (a) Malwitz MA, Lim SH, White-Morris RL, Pham DM, Olmstead MM, Balch AL (2012) Crystallization and interconversions of vapor-sensitive, luminescent polymorphs of [(C6H11NC)2AuI](AsF6) and [(C6H11NC)2AuI](PF6). J Am Chem Soc 134:10885–10893. (b) Kiri P, Hyett G, Binions R (2010) Solid state thermochromic materials. Adv Mat Lett 1:86–105. (c) Wenger OS (2013) Vapochromism in organometallic and coordination complexes: chemical sensors for volatile organic compounds. Chem Rev 113:3686–3733. (d) Ciardelli F, Ruggeri G, Pucci A (2013) Dye-containing polymers: methods for preparation of mechanochromic materials. Chem Soc Rev 42:857–870. (e) Sagara Y, Kato T (2009) Mechanically induced luminescence changes in molecular assemblies. Nat Chem 1:605–610. (f) Balch AL (2009) Dynamic crystals: visually detected mechanochemical changes in the luminescence of gold and other transition-metal complexes. Angew Chem Int Ed 48:2641–2644. (g) Sagara Y, Yamane S, Mitani M, Weder C, Kato T (2016) Mechanoresponsive luminescent molecular assemblies: an emerging class of materials. Adv Mater 28:1073–1095

    Google Scholar 

  2. Park SK, Cho I, Gierschner J, Kim JH, Kim JH, Kwon JE, Kwon OK, Whang DR, Park J-H, An B-K, Park SY (2016) Stimuli-responsive reversible fluorescence switching in a crystalline donor-acceptor mixture film: mixed stack charge-transfer emission versus segregated stack monomer emission. Angew Chem Int Ed 55:203–207

    Article  CAS  Google Scholar 

  3. (a) Mutai T, Satou H, Araki K (2005) Reproducible on–off switching of solid-state luminescence by controlling molecular packing through heat-mode interconversion. Nat Mater 4:685–687. (b) Li FF, Zhang L, Gong LL, Yan CS, Gao HY, Luo F (2017) Reversible photo/thermoswitchable dual-color fluorescence through single-crystal-to-single-crystal transformation. Dalton Trans 46:338–341. (c) Lim SH, Olmstead MM, Balch AL (2013) Inorganic topochemistry. Vapor-induced solid state transformations of luminescent, three-coordinate gold(I) complexes. Chem. Sci. 4:311–318. (d) Zeng M-H, Tan Y-X, He Y-P, Yin Z, Chen Q, Kurmoo M (2013) A porous 4-fold-interpenetrated chiral framework exhibiting vapochromism, single-crystal-to-single-crystal solvent exchange, gas sorption, and a poisoning effect. Inorg Chem 52:2353–2360. (e) Huang R-W, Wei Y-S, Dong X-Y, Wu X-H, Du C-X, Zang S-Q, Mak TCW (2017) Hypersensitive dual-function luminescence switching of a silver-chalcogenolate cluster-based metal–organic framework. Nat Chem 9:689–697. (f) Lim SH, Olmstead MM, Balch AL (2011) Molecular accordion: vapoluminescence and molecular flexibility in the orange and green luminescent crystals of the dimer, Au2(μ-bis-(diphenylphosphino)ethane)2Br2. J Am Chem Soc 133:10229–10238. (g) Seki T, Sakurada K, Muromoto M, Ito H (2015) Photoinduced single-crystal-to-single-crystal phase transition and photosalient effect of a gold(I) isocyanide complex with shortening of intermolecular aurophilic bonds. Chem Sci 6:1491–1497

    Google Scholar 

  4. (a) Naumov P, Bharadwaj PK (2015) Single-crystal-to-single-crystal transformations. CrystEngComm 17:8775–8775. (b) Chaudhary A, Mohammad A, Mobin SM (2017) Recent advances in single-crystal-to-single-crystal transformation at the discrete molecular level. Cryst Growth Des 17:2893–2910

    Google Scholar 

  5. (a) Ito H, Muromoto M, Kurenuma S, Ishizaka S, Kitamura N, Sato H, Seki T (2013) Mechanical stimulation and solid seeding trigger single-crystal-to-single-crystal molecular domino transformations. Nat Commun 4:2009. Seki T, Sakurada K, Ito H (2013) Controlling mechano- and seeding-triggered single-crystal-to-single-crystal phase transition: molecular domino with a disconnection of aurophilic bonds. Angew Chem Int Ed 52:12828–12832. (c) Seki T, Sakurada K, Muromoto M, Seki S, Ito H (2016) Detailed investigation of the structural, thermal, and electronic properties of gold isocyanide complexes with mechano-triggered single-crystal-to-single-crystal phase transitions. Chem Eur J 22:1968–1978. (d) Liu G, Liu J, Liu Y, Tao X (2014) Oriented single-crystal-to-single-crystal phase transition with dramatic changes in the dimensions of crystals. J Am Chem Soc 136:590–593. (e) Karothu DP, Weston J, Desta IT, Naumov P (2016) Shape-memory and self-healing effects in mechanosalient molecular crystals. J Am Chem Soc 138:13298–13306

    Google Scholar 

  6. (a) Liu GF, Liu J, Ye X, Nie LN, Gu PY, Tao XT, Zhang QC (2017) Self-healing behavior in a thermo-mechanically responsive cocrystal during a reversible phase transition. Angew Chem Int Ed 56:198–202. (b) Takamizawa S, Miyamoto Y (2014) Superelastic organic crystals. Angew Chem Int Ed 53:6970–6973. (c) Takasaki Y, Takamizawa S (2015) Reversible crystal deformation of a single-crystal host of copper(II) 1-naphthoate-pyrazine through crystal phase transition induced by methanol vapor sorption. Chem Commun 51:5024–5027. (d) Takamizawa S, Takasaki Y (2015) Superelastic shape recovery of mechanically twinned 3,5-difluorobenzoic acid crystals. Angew Chem Int Ed 54:4815–4817

    Google Scholar 

  7. Seki T, Takamatsu Y, Ito H (2016) A screening approach for the discovery of mechanochromic gold(I) isocyanide complexes with crystal-to-crystal phase transitions. J Am Chem Soc 138:6252–6260

    Article  CAS  Google Scholar 

  8. Hong Y, Lam JWY, Tang BZ (2011) Aggregation-induced emission. Chem Soc Rev 40:5361–5388

    Article  CAS  Google Scholar 

  9. Seki T, Tokodai N, Omagari S, Nakanishi T, Hasegawa Y, Iwasa T, Taketsugu T, Ito H (2017) Luminescent mechanochromic 9-anthryl gold(I) isocyanide complex with an emission maximum at 900 nm after mechanical stimulation. J Am Chem Soc 139:6514–6517

    Article  CAS  Google Scholar 

  10. (a) Centore R, Fusco S, Capone F, Causà M (2016) Competition between polar and centrosymmetric packings in molecular crystals: analysis of actual and virtual structures. Cryst Growth Des 16:2260–2265. (b) Myerson AS (1999) Molecular modeling applications in crystallization. Cambridge University Press, Cambridge, pp 207–209

    Google Scholar 

  11. Sheldrick GM (2015) SHELXT. Program for the refinement of crystal structures. University of Göttingen, Göttingen, Germany

    Google Scholar 

  12. Frisch MJ et al (2009) Gaussian 09 Revision C.01. Gaussian Inc, Wallingford, CT

    Google Scholar 

  13. Spartan’10. Wavefunction, Inc, Irvine, CA

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mingoo Jin .

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

Jin, M. (2020). Mechanical-Stimulation-Triggered and Solvent-Vapor-Induced Reverse Single-Crystal-to-Single-Crystal Phase Transitions with Alterations of the Luminescence Color. In: Novel Luminescent Crystalline Materials of Gold(I) Complexes with Stimuli-Responsive Properties. Springer Theses. Springer, Singapore. https://doi.org/10.1007/978-981-15-4063-9_5

Download citation

Publish with us

Policies and ethics