Multiple stimulus-responsive behavior of a triphenylamine-substituted acylhydrazone derivative

A triphenylamine-based acylhydrazone derivative (TBHM) was synthesized, and its emission properties either in solution or in the solid state were studied. It was demonstrated that TBHM showed a significant solvation effect, and the TBHM solution exhibited a very strong fluorescence quenching effect in the presence of iron ions with the detection limit of 9.7 × 10−7 M. In addition, TBHM displayed reversible blue and cyan emissions upon being ground and annealed. Furthermore, TBHM exhibited significant reversible acid/base induced fluorescence conversion characteristics in both organogel and xerogel states due to the protonation effect.

[1]  Liyu Wu,et al.  Reversible fluorescent switching properties of pyrene-substituted acylhydrazone derivatives toward mechanical force and acid vapor with aggregation-induced emission , 2020 .

[2]  B. K. Kanungo,et al.  Photophysical Studies of a Catechol Based Polyfunctional Dipodal Chelator: Application for Optical Probe for Selective Detection of Fe(III) , 2020, Journal of Fluorescence.

[3]  F. E. Suliman,et al.  Photophysical and theoretical studies on the solvatochromic effects and dipole moments evaluation of substituted 1-phenyl-3-naphthyl-5- (4-ethyl benzoate)-2-pyrazoline , 2020 .

[4]  Yongxin Chang,et al.  A novel near-infrared turn-on fluorescent probe for the detection of Fe3+ and Al3+ and its applications in living cells imaging. , 2020, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[5]  Ji-ting Hou,et al.  Design of large π-conjugated α-cyanostilbene derivatives as colorimetric sensors for volatile acids and organic amine gases , 2020 .

[6]  Chunxue Zhang,et al.  Multistimuli-Responsive Fluorescent Organogelator Based on Triphenylamine-Substituted Acylhydrazone Derivative , 2020, ACS omega.

[7]  Liyu Wu,et al.  Stimuli-responsive fluorescence switching: Aggregation-induced emission (AIE), protonation effect and reversible mechanofluochromism of tetraphenylethene hydrazone-based dyes , 2020 .

[8]  Xingliang Liu,et al.  Reversible solid-state mechanochromic luminescence originated from aggregation-induced enhanced emission-active Donor−Acceptor cruciform luminophores containing triphenylamine , 2019 .

[9]  Yilin Chen,et al.  A colorimetric and fluorescent sensor for the detection of both fluoride ions and trifluoroacetic acid based on acylhydrazone derivatives. , 2019, Soft matter.

[10]  Lingyun Wang,et al.  A multistimuli-responsive fluorescent switch in the solution and solid states based on spiro[fluorene-9,9′-xanthene]-spiropyran , 2019, Journal of Materials Chemistry C.

[11]  Yilin Chen,et al.  A mechano-responsive fluorescent xerogel based on an anthracene-substituted acylhydrazone derivative , 2019, New Journal of Chemistry.

[12]  Aiping Gao,et al.  Continuous multi-channel sensing of volatile acid and organic amine gases using a fluorescent self-assembly system , 2019, Journal of Materials Chemistry C.

[13]  Haitao Wang,et al.  Multi-stimuli-responsive fluorescent switching properties of anthracene-substituted acylhydrazone derivative , 2018, Sensors and Actuators B: Chemical.

[14]  Huichao Zhu,et al.  Branched triphenylamine luminophores: Aggregation-induced fluorescence emission, and tunable near-infrared solid-state fluorescence characteristics via external mechanical stimuli , 2018 .

[15]  H. Gul,et al.  Solvent and substituent effect on the photophysical properties of pyrazoline derivatives: A spectroscopic study , 2018 .

[16]  Hongwei Ma,et al.  Novel Fe3+ fluorescence probe based on the charge-transfer (CT) molecules , 2018 .

[17]  R. Lu,et al.  Aggregation-induced emission nanofiber as a dual sensor for aromatic amine and acid vapor , 2017 .

[18]  Pengchong Xue,et al.  Self-assembly of a fluorescent galunamide derivative and sensing of acid vapor and mechanical force stimuli , 2017 .

[19]  K. Müllen,et al.  A dendrimer-based highly sensitive and selective fluorescence-quenching sensor for Fe(3+) both in solution and as film. , 2016, Biosensors & bioelectronics.

[20]  R. Lu,et al.  Recent progress in the mechanochromism of phosphorescent organic molecules and metal complexes , 2016 .

[21]  R. Lu,et al.  Mechanical force-induced luminescence enhancement and chromism of a nonplanar D–A phenothiazine derivative , 2016 .

[22]  T. He,et al.  A BODIPY derivative for colorimetric and fluorometric sensing of fluoride ion and its logic gates behavior , 2015 .

[23]  C. Zhang,et al.  Multicolored-fluorescence switching of ICT-type organic solids with clear color difference: mechanically controlled excited state. , 2015, Chemistry.

[24]  Dong‐sheng Li,et al.  Polymorphism-dependent and piezochromic luminescence based on molecular packing of a conjugated molecule , 2014 .

[25]  Li-juan Wang,et al.  Multi-stimuli responsive fluorescence switching: the reversible piezochromism and protonation effect of a divinylanthracene derivative , 2013 .

[26]  Cheng Gu,et al.  Mechanochromic and thermochromic fluorescent properties of cyanostilbene derivatives , 2013 .

[27]  Xiao Wei,et al.  A highly selective fluorescent sensor for Fe3+ based on covalently immobilized derivative of naphthalimide. , 2013, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[28]  Jia-rui Xu,et al.  Recent advances in mechanochromic luminescent metal complexes , 2013 .

[29]  Li-juan Wang,et al.  Remarkable fluorescence change based on the protonation-deprotonation control in organic crystals. , 2013, Chemical communications.

[30]  Soo Young Park,et al.  Unique Piezochromic Fluorescence Behavior of Dicyanodistyrylbenzene Based Donor–Acceptor–Donor Triad: Mechanically Controlled Photo‐Induced Electron Transfer (eT) in Molecular Assemblies , 2012, Advanced materials.

[31]  J. Tae,et al.  Rhodamine-hydroxamate-based fluorescent chemosensor for FeIII , 2007 .