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.
References
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
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
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
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
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
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
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
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
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
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
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
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
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
Figueira-Duarte TM, Mullen K. Pyrene-based materials for organic electronics. Chem Rev, 2011, 111(11):7260–7314
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
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
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
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
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
Hong YN, Lam JWY, Tang BZ. Aggregation-induced emission: Phenomenon, mechanism and applications. Chem Commun, 2009, 29):4332–4353
Hong YN, Lam JWY, Tang BZ. Aggregation-induced emission. Chem Soc Rev, 2011, 40(11):5361–5388
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
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
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
Li Z. New progress in aggregation-induced emission research. Chin Sci Bull, 2010, 55(26):2924–2925
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
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
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
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
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
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
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
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
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
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
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
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
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
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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