Self-reversible thermofluorochromism of D–A–D triphenylamine derivatives and the effect of molecular conformation and packing

  title={Self-reversible thermofluorochromism of D–A–D triphenylamine derivatives and the effect of molecular conformation and packing},
  author={Anup K. Kundu and Subramanian Vedhanarayanan Karthikeyan and Dohyun Moon and Savarimuthu Philip Anthony},
Triphenylamine (TPA) based donor–acceptor–donor (D–A–D) compounds were synthesized showing aggregation enhanced emission (AEE) and molecular conformation and packing dependent rare self-reversible thermofluorochromism in the solid state. 1, with TPA substituted with phenylenediacetonitrile at both ends, displayed a twisted molecular conformation, whereas OCH3 substitution at the ortho position of TPA (3-MTPA, 2) resulted in a twisted conformation at one end and a coplanar conformation at the… Expand
Excited state intramolecular proton transfer induced fluorescence in triphenylamine molecule: Role of structural conformation and reversible mechanofluorochromism
Abstract Triphenylamine (TPA) based Schiff base molecules (1–4) were synthesized and role of molecular structure and conformation on excited state intramolecular proton transfer (ESIPT) inducedExpand
Unusual fluorescent photoswitching of imidazole derivatives: the role of molecular conformation and twist angle controlled organic solid state fluorescence.
Structural insight is provided for designing a new type of fluorescent organic molecular photoswitches based on conformational modulation that could be of potential interest in optoelectronic devices. Expand
Solvatochromism and mechanochromism observed in a triphenylamine derivative.
  • Chunyang Guo, Qi Zhang, +4 authors X. Mei
  • Medicine, Chemistry
  • Acta crystallographica Section B, Structural science, crystal engineering and materials
  • 2019
Based on structural analyses and theoretical calculations, it is found that intra- and intermolecular CT processes play a key role in the diversity of fluorescent properties. Expand
Temperature-Controlled Locally Excited and Twisted Intramolecular Charge-Transfer State-Dependent Fluorescence Switching in Triphenylamine–Benzothiazole Derivatives
Understanding is provided and opportunity to make use of D–A organic molecules in the LE and TICT states for achieving fluorescence switching and tuning and Computational studies provided further insights into the fluorescence tuning and switching. Expand
ESIPT-active multi-color aggregation-induced emission features of triphenylamine–salicylaldehyde-based unsymmetrical azine family
The development of multi-color aggregation-induced emission (AIE)-featured azine molecules with excited-state intramolecular proton transfer (ESIPT) characteristics has drawn significant interest inExpand
Optoelectronic properties of (Z)-3-(4-(4,5-diphenyl-1H-imidazole-2-yl)phenyl)-2-phenylacrylonitrile films under acid and thermal environments for tuning OLED emission
Abstract A systematic study of changes on optoelectronic properties of (Z)-3-(4-(4,5-diphenyl-1H-imidazole-2-yl)phenyl)-2-phenylacrylonitrile (DPimdPPA) based films owing to treatments with acid orExpand
Flexible control of excited state transition under pressure/temperature: distinct stimuli-responsive behaviours of two ESIPT polymorphs
  • Aisen Li, Hao Liu, +6 authors Weiqing Xu
  • Materials Science
  • Materials Chemistry Frontiers
  • 2019
The conversion between normal emission and ESIPT can be successfully achieved under pressure and temperature.
Triphenylamine-based stimuli-responsive solid state fluorescent materials
Smart fluorescent materials exhibit a controlled fluorescence response to different external stimuli such as pressure, heat, light, pH, etc. Molecular structure and supramolecular assembly via weakExpand
Synthesis of Strongly Fluorescent Imidazole Derivatives: Structure Property Studies, Halochromism and Fluorescent Photoswitching
The present studies attempted to develop new fluorescent molecules and establish structure-property relationship for designing fluorescence switching materials and a rare fluorescence photoswitching in chloroform have been observed with triphenylamine-imidazole derivatives. Expand
A triphenylamine-functionalized luminescent sensor for efficient p-nitroaniline detection.
Following a new detection route, vapor-sensing experiments using a saturated ethanol solution of nitroaromatic isomers have been established for the first time and the title phase showed superior sensitivity towards p-nitroaniline (p-NA) with a low detection limit. Expand


Self-Reversible Mechanochromism and Thermochromism of a Triphenylamine-Based Molecule: Tunable Fluorescence and Nanofabrication Studies
A triphenylamine-based fluorophore, 4-((4-methoxyphenyl)(phenyl)amino)benzaldehyde (1), exhibits external-stimuli-responsive self-reversible solid-state fluorescence switching, tunable fluorescence,Expand
Molecular Engineering of Triphenylamine Based Aggregation Enhanced Emissive Fluorophore: Structure-Dependent Mechanochromism and Self-Reversible Fluorescence Switching
Triphenylamine (TPA), a propeller-shaped optoelectronic molecule, has been used to generate stimuli-responsive smart fluorescent organic materials and correlate the effect of subtle structuralExpand
Multi-Stimulus-Responsive Fluorescent Properties of Donor-π-Acceptor Indene-1,3-dionemethylene-1,4-dihydropyridine Derivatives
Three donor (D)-π-acceptor (πA) indene-1,3-dionemethylene-1,4-dihydropyridine (IDM-DHP) derivatives with triphenylamine (TPA)/bis(diphenylamino)triphenylamine (BDPA-TPA) end groups were designed andExpand
Reversible fluorescence switching and topochemical conversion in an organic AEE material: polymorphism, defection and nanofabrication mediated fluorescence tuning
2-(4-(Diphenylamino)-2-methoxybenzylidene) malononitrile (DPAMBM), an organic aggregation enhanced emission material, showed an external stimulus mediated reversible phase change (crystalline toExpand
Effect of cyano-substitution in distyrylbenzene derivatives on their fluorescence and electroluminescence properties
Efficient organic electroluminescent materials with both high solid-state fluorescence efficiency and high excitons usage efficiency for use in organic light-emitting diodes (OLEDs) are relativelyExpand
Polymorph-dependent solid-state fluorescence and selective metal-ion-sensor properties of 2-(2-hydroxyphenyl)-4(3H)-quinazolinone.
Tunable solid-state fluorescence and selective metal-ion-sensor properties were demonstrated in a single organic material. Expand
Effect of stacking mode on the mechanofluorochromic properties of 3-aryl-2-cyano acrylamide derivatives
Three structurally simple 3-aryl-2-cyano acrylamide derivatives, 2-cyano-3-(2-methoxyphenyl)-2-propenamide (1), 2-cyano-3-(3-methoxyphenyl)-2-propenamide (2) andExpand
Multiple stimuli-responsive and reversible fluorescence switches based on a diethylamino-functionalized tetraphenylethene
Tetra(4-(diethylamino)phenyl)ethene (TPE-4N), a new derivative of tetraphenylethene (TPE), is facilely prepared in one step from bis(4-(diethylamino)phenyl)methanone in a good yield of 85%. TPE-4NExpand
β-Iminoenolate boron complex with terminal triphenylamine exhibiting polymorphism and mechanofluorochromism
A new β-iminoenolate boron complex with a terminal triphenylamine (TP) was synthesized, and it could emit strong fluorescence in solutions and in solid states. Two types of crystals were obtained viaExpand
Halochromic Isoquinoline with Mechanochromic Triphenylamine: Smart Fluorescent Material for Rewritable and Self-Erasable Fluorescent Platform.
Rewritable and self-erasable fluorescent platform has been achieved by make use of unusual fluorescence responses of PQPBA/TQPA with TFA/HCl after exposing NH3. Expand