Phenothiazines with a dimesityl boron moiety, a new class of aminoboranes with B−N linkage, were synthesized. These aminoboranes exhibited interesting photophysical behavior including aggregation-induced emission (AIE), mechanochromism (MC), mechanoluminescence (ML), and a mega Stokes shift (up to 312 nm in hexane). The solid-state emission of the aminoboranes could be switched reversibly by grinding–fuming processes. Furthermore, the phenothiazine derivative with a bromo and an arylborane group at 3- and 7-positions exhibited bright mechanoluminescence. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Sundargopal Ghosh

Department Of Chemistry

C. Arivazhagan

Kirubakaran Bakthavachalam

Arijit Jana

Suraj Kumar Panigrahi

Conformations

Insecticides

AGGREGATION-INDUCED EMISSIONS

AMINOBORANES

MECHANOCHROMISM

PHENOTHIAZINE DERIVATIVES

PHOTOPHYSICAL BEHAVIOR

Solid state emission

Stokes shift

TRIBOLUMINESCENCE

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Chemistry - A European Journal

Designing intramolecular charge-transfer (ICT)-based luminogenic ordered assemblies exhibiting significant electrical transport is a challenging task in the field of organic optoelectronics. In this context, a series of novel phenothiazine-based oligo(p-phenylenevinylene) (OPV1-6) derivatives were designed and their structure–property relationship was investigated. Upon examining their photophysical properties, all the OPVs were found to exhibit significant intramolecular charge-transfer characteristics in organic solvents. While inspecting the self-assembly behaviour, the OPV with a long alkyl chain on the central phenyl core (OPV4) underwent gelation in organic solvent mixtures through strong hydrophobic interactions of the long hexadecyl chains and π-interactions from their aromatic counterparts. Computational studies revealed a lamellar packing of molecules in the assembly. Interestingly, the degree of ICT and the gelation abilities of OPVs were significantly influenced by the electronic nature of the substituents appended to the peripheral phenothiazines. Further, the AC impedance results revealed an increase in storage and electronic transport for the fluorescent thin films prepared by an increase in the content of OPV4 in PMMA. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Phenothiazine-Based Oligo(p-phenylenevinylene)s: Substituents Affected Self-Assembly, Optical Properties, and Morphology-Induced Transport

Four new novel donor–acceptor (A-π-D-A, A-D-π-D-A) compounds (1 a, 1 b, 2 a and 2 b) based on ethylenedioxythiophene (EDOT) and phenothiazine (PTz) have been rationally designed and synthesized towards solid state emission ranging from yellow to near infrared (NIR). The compounds 1 b and 2 b, in thin film form, showed an emission maximum at 713 nm and 696 nm, respectively, with the corresponding absolute solid-state quantum yield of 3.3 % and 9.0 %. The fluorophores showed high emission in the doped state as well when dispersed in polystyrene (PS) matrix with emission maximum ranging from 536 nm to 648 nm with quantum yield in the range 12.4 %–64.4 %. The presence of dicyanovinyl (DCV) group in both the fluorophores was exploited towards cyanide sensing in DMSO leading to turn-on fluorescence emission with high selectivity and sensitivity for cyanide ion with a detection limit of as low as 0.32 μm (8 ppb) for 1 b and 0.57 μm (14 ppb) for 2 b. DFT and TTDFT calculations suggested that the addition of cyanide ion prevented the intramolecular charge transfer (ICT) from the donor (PTz or EDOT) to acceptor (DCV), thereby turning the fluorescence “On”. Using fluorescent spectral and color switching, we have explored logic gates with single and two input signal amplification by applying chemical and light inputs in the form of CN− ion and UV. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Phenothiazine Based Donor–Acceptor Compounds with Solid-State Emission in the Yellow to NIR Region and Their Highly Selective and Sensitive Detection of Cyanide Ion in ppb Level

Phenothiazinyl Boranes: A New Class of AIE Luminogens with Mega Stokes Shift, Mechanochromism, and Mechanoluminescence

A set of triazole-based chromogenic and fluorescent chemosensors with amino acid/carbohydrate-fluorophore conjugates have been designed and synthesized. The metal cation-sensing properties of glycine-anthracene, C24H 24O4N4 (3), glycine-pyrene C26H 24O4N4 (4), glucose-anthracene, C 32H33O10N3 (5) and glucose-pyrene, C34H33O10N3 (6) bio-conjugates have been studied systematically. The significant changes in their absorption spectra are accompanied by a strong color change from light yellow to brown for 3 and 4 and colorless to greenish blue for 5 and 6. Receptors 3 and 4 have potential in the "naked eye" detection of Cu2+ and 5 and 6 for Pb 2+/Hg2+ ion. The receptors 3 and 4 show fluorescence diminution following Cu2+ coordination within the limit of detection at 0.89 parts per billion (ppb) and this is unprecedented, whereas the receptors 5 and 6 present drastic fluorescence quenching upon addition of Hg2+ and Pb2+ within the limit of detection at 4 and 2 ppb respectively. Interestingly, their fluorescence and colorimetric responses are preserved in the presence of water that can be used for the selective colorimetric detection of these ions in aqueous environments. Along with the spectroscopic data, combined 1H NMR titration of the complexes and the DFT studies suggest the proposed coordination modes. © 2014 The Royal Society of Chemistry.

Fulltext

RSC Advances

Synthesis of triazole linked fluorescent amino acid and carbohydrate bio-conjugates: A highly sensitive and skeleton selective multi-responsive chemosensor for Cu(ii) and Pb(ii)/Hg(ii) ions

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Journal	Data powered by TypesetChemistry - A European Journal
Publisher	Data powered by TypesetWiley-VCH Verlag
ISSN	09476539
Open Access	No