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Switching the emission of di(4-ethoxyphenyl)dibenzofulvene among multiple colors in the solid state

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  • Special Topic Aggregated-Induced Emission
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Abstract

Luminescent materials exhibiting emission switching in the solid state have drawn much attention though there is still no clear design strategy for such materials. In this letter, we reported the crystallization induced emission enhancement (CIEE) of di(4-ethoxyphenyl)dibenzofulvene (1), and achieved switching its emission among four different colors through modulation of its molecular packing patterns. We have investigated its potential application as optical recording materials. The twisted conformations of CIEE compounds afford morphology dependent emission and facilitate tuning their emission through modulation of molecular packing patterns. Thus we provide a possible design strategy for solid stimulus responsive luminescent materials.

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References

  1. Wang JA, Mei J, Qin AJ, Sun JZ, Tang BZ. Stimulus responsive fluorescent hyperbranched polymers and their applications. Sci China Chem, 2010, 53(12):2409–2428

    Article  CAS  Google Scholar 

  2. Dou CD, Li D, Zhang HY, Gao HZ, Zhang JY, Wang Y. Ultrasound responsive organogels based on cholesterol-appended quinacridone derivatives with mechanochromic behaviors. Sci China Chem, 2011, 54(4):641–650

    Article  CAS  Google Scholar 

  3. Yamane S, Sagara Y, Mutai T, Araki K, Kato T. Mechanochromic luminescent liquid crystals based on a bianthryl moiety. J Mater Chem C, 2013, 1(15):2648–2656

    Article  CAS  Google Scholar 

  4. Xu BJ, Xie MY, He JJ, Xu B, Chi ZG, Tian WJ, Jiang L, Zhao FL, Liu SW, Zhang Y, Xu ZZ, Xu JR. An aggregation-induced emission luminophore with multi-stimuli single- and two-photon fluorescence switching and large two-photon absorption cross section. Chem Commun, 2013, 49(3):273–275

    Article  CAS  Google Scholar 

  5. Teng MJ, Jia XR, Yang S, Chen XF, Wei Y. Reversible tuning luminescent color and emission intensity: A dipeptide-based light-emitting material. Adv Mater, 2012, 24(9):1255–1261

    Article  CAS  Google Scholar 

  6. Teng MJ, Jia XR, Chen XF, Wei Y. A dipeptide-based multicolored-switching luminescent solid material: When molecular assemblies meet mechanochemical reaction. Angew Chem Int Ed Engl, 2012, 51(26):6398–6401

    Article  CAS  Google Scholar 

  7. Zhao YF, Gao HZ, Fan Y, Zhou TL, Su ZM, Liu Y, Wang Y. Thermally induced reversible phase transformations accompanied by emission switching between different colors of two aromatic-amine compounds. Adv Mater, 2009, 21(31):3165–3169

    Article  CAS  Google Scholar 

  8. Mutai T, Satou H, Araki K. Reproducible on-off switching of solid-state luminescence by controlling molecular packing through heat-mode interconversion. Nat Mater, 2005, 4(9):685–687

    Article  CAS  Google Scholar 

  9. Wei RR, Song PS, Tong AJ. Reversible thermochromism of aggregation-induced emission-active benzophenone azine based on polymorph-dependent excited-state intramolecular proton transfer fluorescence. J Phys Chem C, 2013, 117(7):3467–3474

    Article  CAS  Google Scholar 

  10. Wang YL, Liu W, Bu LY, Li JF, Zheng M, Zhang DT, Sun MX, Tao Y, Xue SF, Yang WJ. Reversible piezochromic luminescence of 9, 10-bis(N-alkylcarbazol-3-yl)vinyl anthracenes and the dependence on N-alkyl chain length. J Mater Chem C, 2013, 1(4):856–862

    Article  CAS  Google Scholar 

  11. Zhang X, Chi Z, Xu B, Chen C, Zhou X, Zhang Y, Liu S, Xu J. End-group effects of piezofluorochromic aggregation-induced enhanced emission compounds containing distyrylanthracene. J Mater Chem, 2012, 22(35):18505–18513

    Article  CAS  Google Scholar 

  12. Chi Z, Zhang X, Xu B, Zhou X, Ma C, Zhang Y, Liu S, Xu J. Recent advances in organic mechanofluorochromic materials. Chem Soc Rev, 2012, 41(10):3878–3896

    Article  CAS  Google Scholar 

  13. Qi Q, Liu Y, Fang X, Zhang Y, Chen P, Wang Y, Yang B, Xu B, Tian W, Zhang SXA. AIE (AIEE) and mechanofluorochromic performances of TPE-methoxylates: Effects of single molecular conformations. RSC Advances, 2013, 3(21):7996–8002

    Article  CAS  Google Scholar 

  14. Figueira-Duarte TM, Mullen K. Pyrene-based materials for organic electronics. Chem Rev, 2011, 111(11):7260–7314

    Article  CAS  Google Scholar 

  15. Qu JQ, Kohl C, Pottek M, Mullen K. Ionic perylenetetracarboxdiimides: Highly fluorescent and water-soluble dyes for biolabeling. Angew Chem Int Ed, 2004, 43(12):1528–1531

    Article  CAS  Google Scholar 

  16. Bell TDM, Bhosale SV, Forsyth CM, Hayne D, Ghiggino KP, Hutchison JA, Jani CH, Langford SJ, Lee MAP, Woodward CP. Melt-induced fluorescent signature in a simple naphthalenediimide. Chem Commun, 2010, 46(27):4881

    Article  CAS  Google Scholar 

  17. Luo JD, Xie ZL, Lam JWY, Cheng L, Chen HY, Qiu CF, Kwok HS, Zhan XW, Liu YQ, Zhu DB, Tang BZ. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem Commun, 2001, (18):1740–1741

    Google Scholar 

  18. Zhao ZJ, Chen SM, Shen XY, Mahtab F, Yu Y, Lu P, Lam JWY, Kwok HS, Tang BZ. Aggregation-induced emission, self-assembly, and electroluminescence of 4,4′-bis(1,2,2-triphenylvinyl)biphenyl. Chem Commun, 2010, 46(5):686–688

    Article  CAS  Google Scholar 

  19. Chan CYK, Lam JWY, Zhao Z, Deng C, Chen S, Lu P, Sung HHY, Kwok HS, Ma Y, Williams ID, Tang BZ. A facile approach to highly efficient and thermally stable solid-state emitters: Knitting up AIE-active TPE luminogens by aryl linkers. ChemPlusChem, 2012, 77(10):949–958

    Article  CAS  Google Scholar 

  20. Hong YN, Lam JWY, Tang BZ. Aggregation-induced emission: Phenomenon, mechanism and applications. Chem Commun, 2009, 29):4332–4353

    Article  Google Scholar 

  21. Hong YN, Lam JWY, Tang BZ. Aggregation-induced emission. Chem Soc Rev, 2011, 40(11):5361–5388

    Article  CAS  Google Scholar 

  22. Wu WB, Ye SH, Huang LJ, Xiao L, Fu YJ, Huang Q, Yu G, Liu YQ, Qin JG, Li QQ, Li Z. A conjugated hyperbranched polymer constructed from carbazole and tetraphenylethylene moieties: Convenient synthesis through one-pot “A(2)+B-4” Suzuki polymerization, aggregation-induced enhanced emission, and application as explosive chemosensors and PLEDs. J Mater Chem, 2012, 22(13):6374–6382

    Article  CAS  Google Scholar 

  23. Wu WB, Ye SH, Tang RL, Huang LJ, Li QQ, Yu G, Liu YQ, Qin JG, Li Z. New tetraphenylethylene-containing conjugated polymers: Facile synthesis, aggregation-induced emission enhanced characteristics and application as explosive chemsensors and PLEDs. Polymer, 2012, 53(15):3163–3171

    Article  CAS  Google Scholar 

  24. Xu XJ, Li JJ, Li QQ, Huang J, Dong YQ, Hong YN, Yan JW, Qin JG, Li Z, Tang BZ. A strategy for dramatically enhancing the selectivity of molecules showing aggregation-induced emission towards biomacromolecules with the aid of graphene oxide. Chem Eur J, 2012, 18(23):7278–7286

    Article  CAS  Google Scholar 

  25. Li Z. New progress in aggregation-induced emission research. Chin Sci Bull, 2010, 55(26):2924–2925

    Article  Google Scholar 

  26. Sun F, Zhang GX, Zhang DQ. A new gelator based on tetraphenylethylene and diphenylalanine: Gel formation and reversible fluorescence tuning. Chin Sci Bull, 2012, 57(33):4284–4288

    Article  CAS  Google Scholar 

  27. Shi JB, Wu Y M, Sun S, Tong B, Zhi JG, Dong YP. Tunable fluorescence conjugated copolymers consisting of tetraphenylethylene and fluorene units: From aggregation-induced emission enhancement to dual-channel fluorescence response. J Polym Sci, Part A: Polym Chem, 2013, 51(2):229–240

    Article  CAS  Google Scholar 

  28. Dong YQ, Lam JWY, Li Z, Qin A J, Tong H, Dong YP, Feng XD, Tang BZ. Vapochromism of hexaphenylsilole. J Inorg Organomet Polym Mater, 2005, 15(2):287–291

    Article  CAS  Google Scholar 

  29. Dong YQ, Lam JWY, Qin AJ, Li Z, Sun JZ, Sung HHY, Williams ID, Tang BZ. Switching the light emission of (4-biphenylyl) phenyldibenzofulvene by morphological modulation: Crystallization-induced emission enhancement. Chem Commun, 2007, 1):40–42

    Article  Google Scholar 

  30. Li C, Luo X, Zhao W, Li C, Liu Z, Bo Z, Dong Y, Dong YQ, Tang BZ. Switching the emission of tetrakis(4-methoxyphenyl)ethylene among three colors in the solid state. New J Chem, 2013, 37(6):1696–1699

    Article  CAS  Google Scholar 

  31. Luo X, Zhao W, Shi J, Li C, Liu Z, Bo Z, Dong YQ, Tang BZ. Reversible switching emissions of tetraphenylethene derivatives among multiple colors with solvent vapor, mechanical, and thermal stimuli. J Phys Chem C, 2012, 116(41):21967–21972

    Article  CAS  Google Scholar 

  32. Luo XL, Li JN, Li CH, Heng LP, Dong YQ, Liu ZP, Bo ZS, Tang BZ. Reversible switching of the emission of diphenyldibenzofulvenes by thermal and mechanical stimuli. Adv Mater, 2011, 23(29):3261–3265

    Article  CAS  Google Scholar 

  33. Gu XG, Yao JJ, Zhang GX, Zhang DQ. Controllable self-assembly of di(p-methoxylphenyl)dibenzofulvene into three different emission forms. Small, 2012, 8(22):3406–3411

    Article  CAS  Google Scholar 

  34. Gu XG, Yao JJ, Zhang GX, Yan YL, Zhang C, Peng Q, Liao Q, Wu YS, Xu ZZ, Zhao YS, Fu HB, Zhang DQ. Polymorphism-dependent emission for di(p-methoxylphenyl)dibenzofulvene and analogues: Optical waveguide/amplified spontaneous emission behaviors. Adv Funct Mater, 2012, 22(23):4862–4872

    Article  CAS  Google Scholar 

  35. Bu LY, Sun MX, Zhang DT, Liu W, Wang YL, Zheng M, Xue SF, Yang WJ. Solid-state fluorescence properties and reversible piezochromic luminescence of aggregation-induced emission-active 9,10-bis(9,9-dialkylfluorene-2-yl)vinyl anthracenes. J Mater Chem C, 2013, 1(10):2028–2035

    Article  CAS  Google Scholar 

  36. Sun XX, Zhang XP, Li XY, Liu SY, Zhang GQ. A mechanistic investigation of mechanochromic luminescent organoboron materials. J Mater Chem, 2012, 22(33):17332–17339

    Article  CAS  Google Scholar 

  37. Gong Y, Tan Y, Liu J, Lu P, Feng C, Yuan WZ, Lu Y, Sun JZ, He G, Zhang Y. Twisted D-[small pi]-A solid emitters: Efficient emission and high contrast mechanochromism. Chem Commun, 2013, 49(38):4009–4011

    Article  CAS  Google Scholar 

  38. Mao WG, Chen K, OuYang M, Sun JW, Zhou YB, Song QB, Zhang C. Synthesis and characterization of new cyanostilbene-based compound exhibiting reversible mechanochromism. Acta Chim Sin, 2013, 71(4):613–618

    Article  CAS  Google Scholar 

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Correspondence to YongQiang Dong.

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Li, C., Luo, X., Zhao, W. et al. Switching the emission of di(4-ethoxyphenyl)dibenzofulvene among multiple colors in the solid state. Sci. China Chem. 56, 1173–1177 (2013). https://doi.org/10.1007/s11426-013-4931-8

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  • DOI: https://doi.org/10.1007/s11426-013-4931-8

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