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Synthesis, Aggregation Induced Emission and Mechanochromic Luminescence of New β-Diketone Derivatives Bearing Tetraphenylene Moieties

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Abstract

A series of β-diketone derivatives bearing tetraphenylene (TPE) moieties were synthesized and characterized. Their photophysical properties were investigated systematically via spectroscopic and theoretical methods. All compounds exhibit broad absorption bands between 300 and 450 nm, which are assigned to the 1π-π* transition of the conjugated system mixed intramolecular charge-transfer (ICT) transitions. Meanwhile, the emission of these compounds in solution at room temperature (λ em = 458 ~ 509 nm) can be attributed to the 1π,π*/1ICT state. Introduction of freely rotatable TPE to conventional β-diketone luminophors quenches their light emissions in the solutions, but endows these molecules with aggregation-induced emission (AIE) characteristics in the condensed phase due to the restriction of intramolecular rotation. The spectroscopic studies and theoretical calculations indicate that the photophysical properties of these β-diketone derivatives can be tuned by the appended substituents, which would be useful for rational design of AIE compounds with high solid state luminescence performance. Furthermore, these AIE-active compounds exhibited distinct piezofluorochromic properties and switched reversibly upon grinding-fuming. Their photophysical properties have been investigated with the aim to provide a basis for elucidating the structure-property correlations and developing new multi-stimuli responsive luminescent materials.

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References

  1. Irie M, Fukaminato T, Sasaki T, Tamai N, Kawai T (2002) Organic chemistry: a digital fluorescent molecular photoswitch. Nature 420:759–760

    Article  CAS  PubMed  Google Scholar 

  2. Kishimura A, Yamashita T, Yamaguchi K, Aida T (2005) Rewritable phosphorescent paper by the control of competing kinetic and thermodynamic self-assembling events. Nat Mater 4:546–549

    Article  CAS  PubMed  Google Scholar 

  3. Sun H, Liu S, Lin W, Zhang KY, Lv W, Huang X, Huo F, Yang H, Jenkins G, Zhang Q, Huang W (2014) Smart responsive phosphorescent materials for data recording and security protection. Nat Commun 5:4601/1–4601/9

    CAS  Google Scholar 

  4. Luo J, Xie Z, Lam JW, Cheng L, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D, Tang BZ (2001) Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem Commun 18:1740–1741

    Article  Google Scholar 

  5. Byeong-Kwan A, Soon-Ki K, Sang-Don J, Soo YP (2002) Enhanced emission and its switching in fluorescent organic nanoparticles. J Am Chem Soc 124:14410–14415

    Article  Google Scholar 

  6. Chen J, Law CC, Lam JW, Dong Y, Lo SM, Williams ID, Zhu D, Tang BZ (2003) Synthesis, light emission, nanoaggregation, and restricted intramolecular rotation of 1,1-substituted 2,3,4,5-tetraphenylsiloles. Chem Mater 15:1535–1546

    Article  CAS  Google Scholar 

  7. Mei J, Hong Y, Lam JW, Qin A, Tang Y, Tang BZ (2014) Aggregation-induced emission: the whole is more brilliant than the parts. Adv Mater 26:5429–5479

    Article  CAS  PubMed  Google Scholar 

  8. 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 

  9. Zolotareva N, Semenov V (2013) β-Diketones and their derivatives in sol-gel processes. Russ Chem Rev 82:964–987

    Article  Google Scholar 

  10. Zhu H, Shi J, Huang Z, Lv L, Duan J (2015) Structures, spectroscopic analysis, herbicidal activities and enamine-aminone tautomerism of new β-diketone derivatives modified with glycylglycine methyl ester. J Mol Struct 1089:170–177

    Article  CAS  Google Scholar 

  11. Kersey FR, Zhang G, Palmer GM, Dewhirst MW, Fraser CL (2010) Stereocomplexed PLA-PEG nanoparticles with dual-emissive boron dyes for tumor accumulation. ACS Nano 4:4989–4996

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Chow XY, Wang S, Cheng X (1993) The Photocycloaddition of dibenzoylmethanatoboron difluoride (DBMBF2) with conjugated enones and en-esters. Can J Chem 71:846–854

    Article  CAS  Google Scholar 

  13. Sun Y, Rohde D, Liu Y, Wan L, Wang Y, Wu W, Di C, Yu G, Zhu D (2006) A novel air-stable n-type organic semiconductor: 4,4′-bis[(6,6′-diphenyl)-2,2-difluoro-1,3,2-dioxaborine] and its application in organic ambipolar field-effect transistors. J Mater Chem 16:4499–4503

    Article  CAS  Google Scholar 

  14. García-Moreno I, Costela A, Campo L, Sastre R, Amat-Guerri F, Liras M, Arbeloa F, Prieto J, Arbeloa I (2004) 8-phenyl-substituted dipyrromethene·BF2 complexes as highly efficient and photostable laser dyes. J Phys Chem A 108:3315–3323

    Article  Google Scholar 

  15. Domercq B, Grasso C, Maldonado JL, Halik M, Barlow S, Marder SR, Kippelen B (2004) Electron-transport properties and use in organic light-emitting diodes of a bis(dioxaborine)fluorene derivative. J Phys Chem B 108:8647–8651

    Article  CAS  Google Scholar 

  16. Qi Q, Zhang J, Xu B, Li B, Zhang SX, Tian W (2013) Mechanochromism and polymorphism-dependent emission of tetrakis(4-(dimethylamino)phenyl)ethylene. J Phys Chem C 117:24997–25003

    Article  CAS  Google Scholar 

  17. Zhang X, Chi Z, Xu B, Chen B, 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 

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

    Article  CAS  Google Scholar 

  19. Luo X, Li J, Li C, Heng L, Dong YX, 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 

  20. Tsuchimoto T, Ozawa Y, Negoro R, Shira-kawa E, Kawakami Y (2004) Zirconium triflate catalyzed direct coupling reaction of lactams with heterocyclic arenes under atmospheric oxygen. Angew Chem Int Ed 43:4231–4233

    Article  CAS  Google Scholar 

  21. Tsuchimoto T, Matsubayashi H, Kaneko M, Nagase Y, Miyamura T, Shirakawa E (2015) Low viscosity allophanates containing actinically curable groups. J Am Chem Soc 46:1492–1503

    Google Scholar 

  22. Tsuchimoto T, Igarashi M, Aoki K (2010) Exclusive synthesis of β-alkylpyrroles under indium catalysis: carbonyl compounds as sources of alkyl groups. Chem Eur J 16:8975–8979

    Article  CAS  PubMed  Google Scholar 

  23. Tsuchi-moto T, Iwabuchi M, Nagase Y, Oki K, Takahashi H (2011) A general and efficient iridium-catalyzed hydroformylation of olefins. Angew Chem Int Ed 50:280–284

    Article  Google Scholar 

  24. Nagase Y, Sugiya-ma T, Nomiyama S, Yonekura K, Tsuchimoto T (2014) Zinc-catalyzed direct cyanation of indoles and pyrroles: nitromethane as a source of a cyano group. Adv Synth Catal 356:347–352

    Article  CAS  Google Scholar 

  25. Zhou C, Larock R (2005) A regio- and stereoselective route to tetrasubstituted olefins by the palladium-catalyzed three-component coupling of aryl iodides, internal alkynes and arylboronic acids. J Organomet Chem 36:3765–3777

    Article  Google Scholar 

  26. Liang G, Lam JY, Qin W, Li J, Xie N, Tang B (2014) Molecular luminogens based on restriction of intramolecular motions through host–guest inclusion for cell imaging. Chem Commun 50:1725–1727

    Article  CAS  Google Scholar 

  27. Frisch MJ, Trucks GW, Schlegel HB, et al. (2010) Gaussian 09, revision B. 01. Gaussian, Inc., Wallingford CT

    Google Scholar 

  28. Hehre WJ, Ditch R, Pople JA (1972) Self-consistent molecular orbital methods. XII Further Extensions of Gaussian-Type Basis Sets for use in Molecular Orbital Studies of Organic Molecules J Chem Phys 56:2257–2261

    CAS  Google Scholar 

  29. Hariharan PC, Pople JA (1973) The influence of polarization functions on molecularorbital hydrogenation energies. Theor Chim Acta 28:213–222

    Article  CAS  Google Scholar 

  30. Francl MM, Pietro WJ, Hehre WJ, Binkley JS, Gordon MS (1982) Self-consistent molecular orbital methods. XXIII A polarization-Type Basis Set for Second-Row Elements J Chem Phys 77:3654–3665

    CAS  Google Scholar 

  31. Sheldrick GM (1997) SHELXS-97: a program for structure determination. University of Gotingen, Germany

    Google Scholar 

  32. Siemens (1996) SHELXTL. Version 5.06. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA

    Google Scholar 

  33. Zhu X, Huang H, Liu R, Jin X, Li Y, Wang D, Wang Q, Zhu H (2015) Aza-boron-diquinomethene complexes bearing N-aryl chromophores: synthesis, crystal structures, tunable photophysics, the protonation effect and their application as pH sensors. J Mater Chem C 3:3774–3782

    Article  CAS  Google Scholar 

  34. Axel DB (1993) Density-functional thermochemistry. III The Role of Exact Exchange J Chem Phys 7:5648–5652

    Google Scholar 

  35. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789

    Article  CAS  Google Scholar 

  36. Gill PMW, Johnson BG, Pople JA (1992) The performance of the Becke-lee-Yang-Parr (B-LYP) density functional theory with various basis sets. Chem Phys Lett 197:499–505

    Article  CAS  Google Scholar 

  37. Krishnan R, Binkley JS, Seeger R, Pople JA (1980) Self-consistent molecular orbital methods. 20. Basis set for correlated wave-functions. J Chem Phys 72:650–654

    Article  CAS  Google Scholar 

  38. Wang D, Liu R, Chen C, Wang S, Chang J, Wu H, Zhu H, Waclawik ER (2013) Synthesis, photophysical and electrochemical properties of aza-boron-diquinomethene complexes. Dyes Pigments 99:240–249

    Article  CAS  Google Scholar 

  39. Liu Y, Guo J, Liu R, Wang Q, Jin X, Ma L, Lv W, Liu S, Yuan S, Zhu H (2015) Synthesis and luminescent properties of 4′-phenyl-2,2′:6′,2′′-terpyridyl compounds bearing different aryl substituents. J Lumin 157:249–256

    Article  CAS  Google Scholar 

  40. Li H, Zhang X, Chi Z, Xu B, Zhou W, Liu S, Zhang Y, Xu J (2011) New thermally stable piezofluorochromic aggregation-induced emission compounds. Org Lett 13:556–559

    Article  PubMed  Google Scholar 

  41. Cui Y, Yin Y, Cao H, Zhang M, Shan G, Sun H, Wu Y, Su Z, Xie W (2015) Efficient piezochromic luminescence from tetraphenylethene functionalized pyridine-azole derivatives exhibiting aggregation-induced emission. Dyes Pigments 119:62–69

    Article  CAS  Google Scholar 

  42. Zhang X, Chi Z, Zhou X, Liu S, Zhang Y, Xu J (2012) Influence of carbazolyl groups on properties of piezofluorochromic aggregation-enhanced emission compounds containing distyrylanthracene. J Phys Chem C 116:23629–23638

    Article  CAS  Google Scholar 

  43. Wang J, Mei J, Hu R, Sun J, Qin A, Tang B (2012) Click synthesis, aggregation-induced emission, E/Z isomerization, self-organization, and multiple chromisms of pure stereoisomers of a tetraphenylethene-cored luminogen. J Am Chem Soc 134:9956–9966

    Article  CAS  PubMed  Google Scholar 

  44. Zhu X, Liu R, Li Y, Huang H, Wang Q, Wang D, Zhu X, Liu S, Zhu H (2014) An AIE-active boron difluoride complex: multi-stimuli-responsive fluorescence and application for data security protection. Chem Commun 50:12951–12954

    Article  CAS  Google Scholar 

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Acknowledgments

We greatly acknowledge the financial support in part by Natural Science Foundation of the Jiangsu Higher Education Institutions of China (13KJB150018), Natural Science Foundation of Jiangsu Province (BK20130926, BK20150123), Jiangsu Planned Projects for Postdoctoral Research Funds (1302089C) and SRF for ROCS, SEM. (R. Liu).

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Authors and Affiliations

  1. Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, 211816, China

    Haijie Shi, Rui Liu, Senqiang Zhu, Qiqi Gong, Xiaolin Zhu & Hongjun Zhu

  2. Jiangsu Vocational College of Information Technology, Wuxi, 214153, China

    Hong Shi

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  1. Haijie Shi
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  2. Rui Liu
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  7. Hongjun Zhu
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Correspondence to Rui Liu or Hongjun Zhu.

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Shi, H., Liu, R., Zhu, S. et al. Synthesis, Aggregation Induced Emission and Mechanochromic Luminescence of New β-Diketone Derivatives Bearing Tetraphenylene Moieties. J Fluoresc 26, 2005–2013 (2016). https://doi.org/10.1007/s10895-016-1894-0

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