Multi‐Stimuli Response Displaying Novel Phenothiazine‐Based Non‐Planar D‐π‐A Hydrazones: Synthesis, Characterization, Photophysical and Thermal studies. Issue 34 (7th December 2017)

• Record Type: Journal Article
• Authors: Sachdeva, Tanisha; Bishnoi, Swati; Milton, Marilyn Daisy
• Is Part Of: ChemistrySelect. Volume 2:Issue 34(2017)
• Page Start: 11307
• Page End: 11313
• Publication Date: 2017-12-07
• Subjects: Acidochromism -- donor-acceptor -- hydrazones -- mechanofluorochromism -- Phenothiazine; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201702684
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Multi‐stimuli responsive non‐planar D‐π‐A hydrazones bearing non‐planar phenothiazine as donor (D ) and benzothiazole and dinitrophenyl rings as acceptor (A ) were synthesized and their structural, photophysical, thermochromic, mechanofluorochromic (MFC) and acidochromic properties were studied. Thermal gravimetric analysis (TGA) and spectrophotometric studies revealed higher thermal stability, better ICT character and enhancedD ‐A intramolecular interactions in phenothiazine hydrazone bearing phenyl pendant ring. Hydrazones bearing benzothiazole ring asA displayed aggregation induced emission enhancement (AIEE) as well as acidochromism in presence of volatile acids like TFA. Greater extent of change in color and emission wavelength under external pressure revealed better MFC behavior of phenothiazine hydrazone bearing phenyl pendant ring. Two of the hydrazones exhibited reversible mechanofluorochromism on fuming their ground samples with DCM vapors. Structure‐property relationship studied by single crystal X‐ray diffraction patterns suggested the existence of twisted molecular conformation and weak intermolecular interactions such as π–π, C‐H–π and S–S which played a vital role in the phase transition from crystalline to amorphous state under mechanical stress which was further justified by powder X‐ray diffraction patterns. Abstract : Multi‐stimuli responsive non‐planar D‐π‐A hydrazones bearing non‐planar phenothiazine as donor (D) and benzothiazole and dinitrophenyl rings as acceptor (A) were synthesized. Their structural, photophysical, thermochromic, piezochromic, mechanofluorochromic (MFC) and acidochromic properties were improved by introducing phenyl ring on phenothiazine hydrazones; displaying potential to be used as solid state sensors, optoelectronic devices as well as smart materials.