Tuning the Electronic Nature of Aggregation-Induced Emission Luminogens with Enhanced Hole-Transporting Property

Triphenylamine (TPA) is a well-known hole-transporting material but suffers aggregation-caused emission quenching in the solid state. Tetraphenylethene (TPE), on the other hand, is an archetypal luminogen that shows the phenomenon of aggregation-induced emission (AIE). In this work, TPA is attached to the TPE core as peripheral group to generate new AIE luminogens with enhanced hole-transporting property. The TPA-TPE adducts, named 1-[4′-(diphenylamino)biphenyl-4-yl]-1,2,2-triphenylethene (TPATPE) and 1,2-bis[4′-(diphenylamino)biphenyl-4-yl]-1,2-diphenylethene (2TPATPE) are synthesized in satisfactory yields by Suzuki coupling of 4-(diphenylamino)phenylboronic acid with 1-(4-bromophenyl)-1,2,2-triphenylethene and 1,2-bis(4-bromophenyl)-1,2-diphenylethene, respectively. Whereas the hybrid molecules are practically nonluminescent in the solution state, their aggregates in poor solvents and thin films emit intensely with fluorescence quantum yields up to 100%. Both TPATPE and 2TPATPE are thermally and morpho...

[1]  J. Mcmurry.  Carbonyl-coupling reactions using low-valent titanium , 1989 .

[2]  J. Kampf,et al.  Intermolecular interactions in pi-stacked conjugated molecules. Synthesis, structure, and spectral characterization of alkyl bithiazole oligomers. , 2003, Journal of the American Chemical Society.

[3]  C. Botta,et al.  Synthesis and crystal structure and optical properties of fluorenic-core oligomers , 2002 .

[4]  Chihaya Adachi,et al.  100% phosphorescence quantum efficiency of Ir(III) complexes in organic semiconductor films , 2005 .

[5]  Shixiong Qian,et al.  Aggregation‐induced Emission (AIE)‐active Starburst Triarylamine Fluorophores as Potential Non‐doped Red Emitters for Organic Light‐emitting Diodes and Cl2 Gas Chemodosimeter , 2007 .

[6]  Limei Sun,et al.  Novel mesogen‐jacketed poly(p‐phenylenevinylene) derivatives bearing oxadiazole pendants: Design, synthesis, and optoelectronic properties , 2008 .

[7]  Yongqiang Dong,et al.  Label-free fluorescent probing of G-quadruplex formation and real-time monitoring of DNA folding by a quaternized tetraphenylethene salt with aggregation-induced emission characteristics. , 2008, Chemistry.

[8]  Y. Shirota.  Organic materials for electronic and optoelectronic devices , 2000 .

[9]  Zhishan Bo,et al.  Toward high molecular weight triphenylamine-based hyperbranched polymers , 2005 .

[10]  C. Hawker,et al.  Self-encapsulation of poly-2,7-fluorenes in a dendrimer matrix. , 2001, Journal of the American Chemical Society.

[11]  Ben Zhong Tang,et al.  Protein detection and quantitation by tetraphenylethene-based fluorescent probes with aggregation-induced emission characteristics. , 2007, The journal of physical chemistry. B.

[12]  S. Yamaguchi,et al.  Intense solid-state blue emission with a small Stokes' shift: pi-stacking protection of the diphenylanthracene skeleton. , 2009, Chemical communications.

[13]  Hoi Sing Kwok,et al.  Aggregation-induced emission, self-assembly, and electroluminescence of 4,4'-bis(1,2,2-triphenylvinyl)biphenyl. , 2010, Chemical communications.

[14]  Ian D. Williams,et al.  Switching the light emission of (4-biphenylyl)phenyldibenzofulvene by morphological modulation: crystallization-induced emission enhancement. , 2007, Chemical communications.

[15]  Khai Leok Chan,et al.  Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices. , 2009, Chemical reviews.

[16]  Sang Ho Lee,et al.  Highly fluorescent solid-state asymmetric spirosilabifluorene derivatives. , 2005, Journal of the American Chemical Society.

[17]  S. Forrest,et al.  Highly efficient phosphorescent emission from organic electroluminescent devices , 1998, Nature.

[18]  Ben Zhong Tang,et al.  Aggregation-induced Emission of Silole Molecules and Polymers: Fundamental and Applications , 2009 .

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

[20]  Norio Miyaura,et al.  Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds , 1995 .

[21]  Yongqiang Dong,et al.  Aggregation-induced emissions of tetraphenylethene derivatives and their utilities as chemical vapor sensors and in organic light-emitting diodes , 2007 .

[22]  G Leising,et al.  Polyfluorenes with polyphenylene dendron side chains: toward non-aggregating, light-emitting polymers. , 2001, Journal of the American Chemical Society.

[23]  B. Tang,et al.  Highly efficient organic light-emitting diodes with a silole-based compound , 2002 .

[24]  Daoben Zhu,et al.  Structures, electronic states, photoluminescence, and carrier transport properties of 1,1-disubstituted 2,3,4,5-tetraphenylsiloles. , 2005, Journal of the American Chemical Society.

[25]  B. Liu,et al.  Conjugated Polyelectrolytes as Light‐Up Macromolecular Probes for Heparin Sensing , 2009 .

[26]  C. Tang,et al.  Organic Electroluminescent Diodes , 1987 .

[27]  Yi Luo,et al.  Aggregation-enhanced luminescence and vibronic coupling of silole molecules from first principles , 2006 .

[28]  X. Tao,et al.  Aggregation-Induced Emissions of Fluorenonearylamine Derivatives : A New Kind of Materials for Nondoped Red Organic Light-Emitting Diodes , 2008 .

[29]  Ben Zhong Tang,et al.  Aggregation-induced emission: phenomenon, mechanism and applications. , 2009, Chemical communications.

[30]  J. Roncali,et al.  From One‐ to Three‐Dimensional Organic Semiconductors: In Search of the Organic Silicon? , 2007 .

[31]  Shui-Tong Lee,et al.  Bipolar Molecule as an Excellent Hole-Transporter for Organic-Light Emitting Devices , 2009 .

[32]  T. Hiyama,et al.  Synthesis, crystal structure, and photophysical properties of (1E,3E,5E)-1,3,4,6-Tetraarylhexa-1,3,5-trienes: a new class of fluorophores exhibiting aggregation-induced emission. , 2009, Chemistry, an Asian journal.

[33]  Sang-Don Jung,et al.  Enhanced emission and its switching in fluorescent organic nanoparticles. , 2002, Journal of the American Chemical Society.

[34]  Yang Liu,et al.  Changing the Behavior of Chromophores from Aggregation‐Caused Quenching to Aggregation‐Induced Emission: Development of Highly Efficient Light Emitters in the Solid State , 2010, Advanced materials.

[35]  G. Bazan,et al.  Collective Response from a Cationic Tetrahedral Fluorene for Label‐Free DNA Detection , 2007 .

[36]  J. Mikroyannidis,et al.  Synthesis, photophysics and electroluminescence of dendronized styryl-substituted fluorene with triphenylamine units , 2009 .

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

[38]  J. N. Moorthy,et al.  Blue light-emitting and hole-transporting amorphous molecular materials based on diarylaminobiphenyl-functionalized bimesitylenes. , 2008, Chemical communications.

[39]  X. Tao,et al.  Intermolecular Hydrogen Bonds Induce Highly Emissive Excimers: Enhancement of Solid-State Luminescence , 2007 .

[40]  J. Qin,et al.  An aggregation-induced blue shift of emission and the self-assembly of nanoparticles from a novel amphiphilic oligofluorene. , 2008, Chemical communications.

[41]  S. Lindeman,et al.  Practical synthesis of unsymmetrical tetraarylethylenes and their application for the preparation of [triphenylethylene-spacer-triphenylethylene] triads. , 2007, The Journal of organic chemistry.

[42]  B. Tang,et al.  Creation of highly efficient solid emitter by decorating pyrene core with AIE-active tetraphenylethene peripheries. , 2010, Chemical communications.

[43]  Yongqiang Dong,et al.  Fluorescent "light-up" bioprobes based on tetraphenylethylene derivatives with aggregation-induced emission characteristics. , 2006, Chemical communications.