High solid-state luminescence in propeller-shaped AIE-active pyridine-ketoiminate-boron complexes.

Two pyridine-ketoiminate-based organoboron complexes (2 and 3) were developed. 2 and 3 showed very weak emission in low-viscosity organic solvents because of the intramolecular rotation induced non-radiative process. Their emission can be dramatically enhanced by the increase in solvent viscosity or by molecular aggregation in the solid state. Moreover, 2 and 3 exhibited intense emission with high quantum yield of 0.53 and 0.46, respectively. X-ray crystallographic analysis showed that the weak intermolecular interactions such as C-H···F and C-H···π by fixing the molecular conformations of 2 and 3 were responsible for intense luminescence in the solid state. The large Stokes shifts and high efficient solid-state emission of 2 and 3 make them valuable AIE luminophores for further potential applications in the fields of fluorescence imaging and materials science.

[1]  Zhenyu Li,et al.  Benzothiazole-enamide-based BF2 complexes: luminophores exhibiting aggregation-induced emission, tunable emission and highly efficient solid-state emission , 2015 .

[2]  Hua Lu,et al.  Asymmetric core-expanded aza-BODIPY analogues: facile synthesis and optical properties. , 2015, Chemical communications.

[3]  J. Duan,et al.  Aggregation-induced emission (AIE) of pyridyl-enamido-based organoboron luminophores. , 2015, Chemical communications.

[4]  Hua Lu,et al.  Synthesis and spectroscopic properties of novel meso-cyano boron-pyridyl-isoindoline dyes. , 2014, Organic & biomolecular chemistry.

[5]  K. Müllen,et al.  Synthesis and optophysical properties of dimeric aza-BODIPY dyes with a push-pull benzodipyrrolidone core. , 2014, Chemical communications.

[6]  Kazuo Tanaka,et al.  Boron diiminate with aggregation-induced emission and crystallization-induced emission-enhancement characteristics. , 2014, Chemistry.

[7]  Hua Lu,et al.  Structural modification strategies for the rational design of red/NIR region BODIPYs. , 2014, Chemical Society reviews.

[8]  Lijuan Jiao,et al.  Facile synthesis of highly fluorescent BF₂ complexes bearing isoindolin-1-one ligand. , 2014, Dalton transactions.

[9]  G. Ulrich,et al.  Luminescent materials: locking π-conjugated and heterocyclic ligands with boron(III). , 2014, Angewandte Chemie.

[10]  Jing Lu,et al.  Synthesis and fluorescence properties of isoindoline–benzazole-based boron difluoride complexes , 2014 .

[11]  Jing Xu,et al.  Boron-pyridyl-imino-isoindoline dyes: facile synthesis and photophysical properties. , 2014, Chemical communications.

[12]  A. Breeze,et al.  Real-Time Monitoring of New Delhi Metallo-β-Lactamase Activity in Living Bacterial Cells by 1H NMR Spectroscopy** , 2014, Angewandte Chemie.

[13]  X. Pu,et al.  Regiospecific N-heteroarylation of amidines for full-color-tunable boron difluoride dyes with mechanochromic luminescence. , 2013, Angewandte Chemie.

[14]  B. Tang,et al.  Aggregation-induced emission and efficient solid-state fluorescence from tetraphenylethene-based N,C-chelate four-coordinate organoborons. , 2013, Chemistry.

[15]  D. Ding,et al.  Bioprobes based on AIE fluorogens. , 2013, Accounts of chemical research.

[16]  G. Ulrich,et al.  2-(2'-Hydroxyphenyl)benzimidazole and 9,10-phenanthroimidazole chelates and borate complexes: solution- and solid-state emitters. , 2013, Organic letters.

[17]  R. Fröhlich,et al.  Fluorescent modular boron systems based on NNN- and ONO-tridentate ligands: self-assembly and cell imaging. , 2013, The Journal of organic chemistry.

[18]  G. Ulrich,et al.  Fluorescent boron(III) iminocoumarins (Boricos). , 2013, Chemical communications.

[19]  Kazuo Tanaka,et al.  Highly emissive boron ketoiminate derivatives as a new class of aggregation-induced emission fluorophores. , 2013, Chemistry.

[20]  Y. Araki,et al.  Pyrrolopyrrole aza-BODIPY analogues: a facile synthesis and intense fluorescence. , 2013, Chemical communications.

[21]  Xiao-Jun Lv,et al.  Aggregation-induced photoluminescent changes of naphthyridine-BF2 complexes. , 2012, Chemistry.

[22]  O. Blacque,et al.  β-Iminoenamine-BF2 complexes: aggregation-induced emission and pronounced effects of aliphatic rings on radiationless deactivation. , 2012, Chemistry, an Asian journal.

[23]  R. Ziessel,et al.  High-performance solution-processed solar cells and ambipolar behavior in organic field-effect transistors with thienyl-BODIPY scaffoldings. , 2012, Journal of the American Chemical Society.

[24]  Xiao-Jun Lv,et al.  Large Stokes shift induced by intramolcular charge transfer in N,O-chelated naphthyridine-BF2 complexes. , 2012, Organic letters.

[25]  M. Matsui,et al.  Synthesis and fluorescence properties of thiazole-boron complexes bearing a β-ketoiminate ligand. , 2012, Organic letters.

[26]  S. Thayumanavan,et al.  Predictably tuning the frontier molecular orbital energy levels of panchromatic low band gap BODIPY-based conjugated polymers , 2012 .

[27]  Tae‐Woo Lee,et al.  Dramatic substituent effects on the photoluminescence of boron complexes of 2-(benzothiazol-2-yl)phenols. , 2012, Chemistry.

[28]  Hua Lu,et al.  Tuning the solid-state luminescence of BODIPY derivatives with bulky arylsilyl groups: synthesis and spectroscopic properties. , 2012, Chemistry.

[29]  Y. Yang,et al.  Aggregation-induced emission in BF2–hydrazone (BODIHY) complexes , 2012 .

[30]  B. Heyne,et al.  High Stokes shift anilido-pyridine boron difluoride dyes. , 2011, Angewandte Chemie.

[31]  M. Matsui,et al.  Synthesis and fluorescence properties of novel pyrazine-boron complexes bearing a β-iminoketone ligand. , 2011, Organic letters.

[32]  Cui‐Hua Zhao,et al.  Solid-state emissive triarylborane-based BODIPY dyes: photophysical properties and fluorescent sensing for fluoride and cyanide ions. , 2011, Organic & biomolecular chemistry.

[33]  Ben Zhong Tang,et al.  Aggregation-induced emission. , 2011, Chemical Society reviews.

[34]  K. Müllen,et al.  Pyrene-based materials for organic electronics. , 2011, Chemical reviews.

[35]  K. Burgess,et al.  Brilliant BODIPY-fluorene Copolymers With Dispersed Absorption and Emission Maxima. , 2011, Macromolecules.

[36]  S. Thayumanavan,et al.  BODIPY-Based Donor–Acceptor π-Conjugated Alternating Copolymers , 2011 .

[37]  Zhenan Bao,et al.  Halogenated Materials as Organic Semiconductors , 2011 .

[38]  Á. Costela,et al.  Difluoro-boron-triaza-anthracene: a laser dye in the blue region. Theoretical simulation of alternative difluoro-boron-diaza-aromatic systems. , 2011, Physical chemistry chemical physics : PCCP.

[39]  M. Matsui,et al.  Strategy for the increasing the solid-state fluorescence intensity of pyrromethene–BF2 complexes , 2010 .

[40]  Jang‐Joo Kim,et al.  Novel binaphthyl-containing bi-nuclear boron complex with low concentration quenching effect for efficient organic light-emitting diodes. , 2010, Chemical communications.

[41]  T. Tsuzuki,et al.  Synthesis and fluorescence properties of a pyridomethene-BF2 complex. , 2010, Organic letters.

[42]  F. Jäkle.  Advances in the synthesis of organoborane polymers for optical, electronic, and sensory applications. , 2010, Chemical reviews.

[43]  P. Choyke,et al.  New strategies for fluorescent probe design in medical diagnostic imaging. , 2010, Chemical reviews.

[44]  B. Tang,et al.  Aggregation-induced emission: phenomenon, mechanism and applications. , 2009, Chemical Communications.

[45]  B. Trofimov,et al.  New Hindered BODIPY Derivatives: Solution and Amorphous State Fluorescence Properties† , 2009 .

[46]  Z. Zuo,et al.  Light harvesting and efficient energy transfer in dendritic systems: new strategy for functionalized near-infrared BF2-azadipyrromethenes. , 2009, Chemistry, an Asian journal.

[47]  E. Akkaya,et al.  Solid-state emissive BODIPY dyes with bulky substituents as spacers. , 2009, Organic letters.

[48]  Yunqi Liu,et al.  Bulky 4-tritylphenylethynyl substituted boradiazaindacene: pure red emission, relatively large Stokes shift and inhibition of self-quenching. , 2008, Chemical communications.

[49]  K. Burgess,et al.  Syntheses of highly fluorescent GFP-chromophore analogues. , 2008, Journal of the American Chemical Society.

[50]  Anthony Harriman,et al.  The chemistry of fluorescent bodipy dyes: versatility unsurpassed. , 2008, Angewandte Chemie.

[51]  X. Qian,et al.  Novel fluorescent fluorine-boron complexes: synthesis, crystal structure, photoluminescence, and electrochemistry properties. , 2008, The Journal of organic chemistry.

[52]  Kevin Burgess,et al.  BODIPY dyes and their derivatives: syntheses and spectroscopic properties. , 2007, Chemical reviews.

[53]  Abhishek P. Kulkarni,et al.  Electron Transport Materials for Organic Light-Emitting Diodes , 2004 .

[54]  G. Ulrich,et al.  Highly efficient energy transfer to a novel organic dye in OLED devices , 2004 .

[55]  Stephen R. Forrest,et al.  White Organic Light‐Emitting Devices for Solid‐State Lighting , 2004 .

[56]  A. W. Addison,et al.  Conversion constants for redox potentials measured versus different reference electrodes in acetonitrile solutions at 25°C , 2000 .

[57]  Xu,et al.  Degradation mechanism of small molecule-based organic light-emitting devices , 1999, Science.

[58]  W. R. Salaneck,et al.  Electroluminescence in conjugated polymers , 1999, Nature.

[59]  G. Köhler,et al.  Excited state properties and deactivation pathways of 7-aminocoumarins , 1994 .

[60]  S. Jenekhe,et al.  Excimers and Exciplexes of Conjugated Polymers , 1994, Science.

[61]  H. C. Longuet-Higgins,et al.  Some Studies in Molecular Orbital Theory I. Resonance Structures and Molecular Orbitals in Unsaturated Hydrocarbons , 1950 .

[62]  L. Brooker,et al.  Steric hindrance to planarity in dye molecules. , 1947, Chemical reviews.

[63]  H S Kwok,et al.  Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. , 2001, Chemical communications.