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Piezoflurochromism and Aggregation Induced Emission Properties of 9, 10-bis (trisalkoxystyryl) Anthracene Derivatives

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Abstract

We report the synthesis of trisalkoxy substituted 9, 10-bis styrylanthracene derivatives (C8-ant and C12-ant) by Heck coupling with very good yield and their photophysical properties. Both C8-ant and C12-ant exhibit aggregation induced emission (AIE), mechnoflurochromism and thermochromism. Trisubstituted 9, 10-distyrylanthracene molecules having all the luminescent properties in a single molecule are first of its kind.

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References

  1. Sagara Y, Kato T (2009) Mechanically induced luminescence changes in molecular assemblies. Nat Chem 1:605–610

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  3. Zhang J, Zou Q, Tian J (2013) Photochromic materials: more than meets the eye. Adv Mater 25:378–399

    Article  CAS  PubMed  Google Scholar 

  4. Dong Y, Lam JWY, Qin A, Liu J, Li Z, Tang BZ, Sun J, Kwok HS (2007) Aggregation-induced emissions of tetraphenylethene derivatives and their utilities as chemical vapor sensors and in organic light-emitting diodes. Appl Phys Lett 91:11111–11113

    Article  Google Scholar 

  5. Liu L, Zhang G, Xiang J, Zhang D, Zhu D (2008) Fluorescence “Turn On” chemosensors for Ag+ and Hg2+ based on tetraphenylethylene motif featuring adenine and thymine moieties. Org Lett 10:4581–4584

    Article  CAS  PubMed  Google Scholar 

  6. Hu XM, Chen Q, Zhou DJ, Cao J, He YJ, Han BH (2011) One-step preparation of fluorescent inorganic–organic hybrid material used for explosive sensing. Polym Chem 2:1124–1128

    Article  CAS  Google Scholar 

  7. Murata H, Kafafi ZH, Uchida M (2002) Efficient organic light emitting diodes with undoped active layers based on silole derivatives. Appl Phys Lett 80:189–191

    Article  CAS  Google Scholar 

  8. Toal SJ, Jones KA, Magde D, Trogler WC (2005) Luminescent silole nanoparticles as chemoselective sensors for Cr (VI). J Am Chem Soc 127:11661–11665

    Article  CAS  PubMed  Google Scholar 

  9. Friend RH, Gymer RW, Holmes AB, Burroughes JH, Marks RN, Taliani C, Bradley DDC, Dos Santos A, Bredas JL, Logdlund M, Salaneck WR (1999) Electroluminescence in conjugated polymers. Nature 397:121–128

    Article  CAS  Google Scholar 

  10. Jenekhe SA, Osaheni JA (1994) Excimers and exciplexes of conjugated polymers. Science 265:765–768

    Article  CAS  PubMed  Google Scholar 

  11. Chen CT (2004) Evolution of red organic light-emitting diodes: materials and devices. Chem Mater 16:4389–4400

    Article  CAS  Google Scholar 

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

  13. An BK, Kwon SK, Jung SD, Park SY (2002) Enhanced emission and its switching in fluorescent organic nanoparticles. J Am Chem Soc 124:14410–14415

    Article  CAS  PubMed  Google Scholar 

  14. Zhang X, Chi Z, Zhang J, Li H, Xu B, Li X, Liu S, Zhang Y, Xu J (2011) Piezofluorochromic properties and mechanism of an aggregation-induced emission enhancement compound containing N-Hexyl-phenothiazine and anthracene moieties. J Phys Chem B 115:7606–7611

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. Dong Y, Xu B, Zhang J, Tan X, Wang L, Chen JH, Wen S, Li B, Ye L, Zou B, Tian W (2012) Piezochromic luminescence based on the molecular aggregation of 9,10-bis((E)-2-(pyrid-2-yl)vinyl)anthracene. Angew Chem Int Ed 51:10782–10785

    Article  CAS  Google Scholar 

  17. Bhongale CJ, Chang CW, Lee CS, Diau EWG, Hsu CS (2005) Relaxation dynamics and structural characterization of organic nanoparticles with enhanced emission. J Phys Chem B 109:13472–13482

    Article  CAS  PubMed  Google Scholar 

  18. An BK, Lee DS, Lee JS, Park YS, Song HS, Park SY (2004) Strongly fluorescent organogel system comprising fibrillar self-assembly of a trifluoromethyl-based cyanostilbene derivative. J Am Chem Soc 126:10232–10233

    Article  CAS  PubMed  Google Scholar 

  19. Chen JW, Xu B, Ouyang XY, Tang BZ, Cao Y (2004) Aggregation-induced emission of cis,cis-1,2,3,4-Tetraphenylbutadiene from restricted intramolecular rotation. J Phys Chem A 108(37):7522–7526

    Article  CAS  Google Scholar 

  20. Funahashi M, Hanna J (1997) Fast hole transport in a new calamitic liquid crystal of 2-(4’-heptyloxyphenyl)-6-Dodecylbenzothiazole. Phys Rev Lett 78:2184–2187

    Article  CAS  Google Scholar 

  21. Schein LB, McGhie AR (1979) Band-hopping mobility transition in naphthalene and deuterated naphthalene. Phys Rev B 20:1631–1639

    Article  CAS  Google Scholar 

  22. Yoon SY, Park SY (2011) Polymorphic and mechanochromic luminescence modulation in the highly emissive dicyanodistyrylbenzene crystal: secondary bonding interaction in molecular stacking assembly. J Mater Chem 21(2011):8338–8346

    Article  CAS  Google Scholar 

  23. Dou C, Han L, Zhao S, Zhang H, Wang Y (2011) Multi-stimuli-responsive fluorescence switching of a donor − acceptor π-conjugated compound. J Phys Chem Lett 2:666–670

    Article  CAS  Google Scholar 

  24. Luo X, Li J, Li C, Heng L, Dong YQ, Liu Z, Bo Z, Tang BZ (2011) Reversible switching of the emission of diphenyldibenzofulvenes by thermal and mechanical stimuli. Adv Mater 23:3261–3265

    Article  CAS  PubMed  Google Scholar 

  25. Zhang X, Chi Z, Xu B, Jiang L, Zhou X, Zhang Y, Liu S, Xu J (2012) Multifunctional organic fluorescent materials derived from 9,10-distyrylanthracene with alkoxyl endgroups of various lengths. Chem Commun 48:10895–10897

    Article  CAS  Google Scholar 

  26. WangY LW, Bu L, Li J, Zheng M, Zhang D, Sun M, Tao Y, Xue S, Yang W (2013) 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 1:856–862

    Article  Google Scholar 

  27. Bu L, Sun M, Zhang D, Liu W, Wang Y, Zheng M, Xue S, Yang W (2013) 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 1(10):2028–2035

    Article  CAS  Google Scholar 

  28. Liu W, Wang Y, Bu L, Li J, Sun M, Zhang D, Zheng M, Yang C, Xue S, Yang W (2013) Chain length-dependent piezofluorochromic behavior of 9,10-bis(p-alkoxystyryl)anthracenes. J Lumin 143:50–55

    Article  CAS  Google Scholar 

  29. He JT, Xu B, Chen FP, Xia HJ, Li KP, Ye L, Tian WJ (2019) Aggregation-induced emission in the crystals of 9, 10-distyrylanthracene derivatives: the essential role of restricted intramolecular torsion. J Phys Chem C 1113:9892–9899

    Google Scholar 

  30. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr., Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Laham MAA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, Revision E.01. Gaussian, Inc., Wallingford

    Google Scholar 

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Acknowledgment

K.D & A.S acknowledge to the financial support of the Council of Scientific and Industrial Research, New Delhi, India (Grant No. 01(2540)/11/EMR-II). R.B & A.S acknowledge to the Department of Science and Technology, New Delhi, India (Grant No. SR/F/1584/2012-13) for the financial support; we acknowledge National Centre for Ultrafast Process, University of Madras, Chennai-113, for providing lifetime measurements.

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Authors and Affiliations

  1. School of Chemistry, Madurai Kamaraj University, Madurai, Tamilnadu, 625 021, India

    Kumaraguru Duraimurugan, Jayaraman Sivamani & Ayyanar Siva

  2. School of Chemistry, Bharathidasan University, Trichirapalli-24, Tamilnadu, India

    Munusamy Sathiyaraj & Viruthachalam Thiagarajan

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  1. Kumaraguru Duraimurugan
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  2. Jayaraman Sivamani
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  3. Munusamy Sathiyaraj
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  4. Viruthachalam Thiagarajan
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  5. Ayyanar Siva
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Correspondence to Ayyanar Siva.

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Duraimurugan, K., Sivamani, J., Sathiyaraj, M. et al. Piezoflurochromism and Aggregation Induced Emission Properties of 9, 10-bis (trisalkoxystyryl) Anthracene Derivatives. J Fluoresc 26, 1211–1218 (2016). https://doi.org/10.1007/s10895-016-1805-4

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  • DOI: https://doi.org/10.1007/s10895-016-1805-4

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