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

Edamana Prasad

Department Of Chemistry

Sundargopal Ghosh

C. Arivazhagan

Sitakanta Satapathy

Arijit Jana

Partha Malakar

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

Charge-transfer (CT) gel materials obtained from low-molecular-weight (LMW) compounds through a supramolecular self-assembly approach have received fascinating attention by many researchers because of their interesting material property and potential applications. However, most of the CT gel materials constructed were of organogels while the construction of CT gels in the form of a hydrogel is a challenge because of the solubility issue in water, which considerably limits the use of CT hydrogels. Herein, for the first time, we report a new LMW gelator [Nα-(fluorenylmethoxycarbonyl)-Nϵ-(δ-butyric-1-pyrenyl)-l-lysine, (FmKPy)], composed of two functional moieties such as fluorenylmethoxycarbonyl and pyrene, which not only parade both hydro and organo (ambidextrous) supramolecular gel formation but also exhibit CT ambidextrous gels when mixed with an electron acceptor such as 2,4,7-trinitro-9-fluorenone (TNF). This finding is significant as the established CT organogelator in the literature did not form an organogel in the absence of an electron acceptor or lose their gelation property upon the addition of the acceptor. CT between pyrene and TNF was confirmed by the color change as well as the appearance of the CT band in the visible region of the absorption spectrum. CT between FmKPy and TNF was supported by the solvent dilution method using tetrahydrofuran as the gel breaker and pyrene fluorescence quenching in the case compound containing pyrene and TNF. The morphology of FmKPy ambidextrous gels indicates the fibrous nature while the self-assembled structure is primarily stabilized by π-π stacking among fluorenyl and pyrenyl moieties and hydrogen bonding between amide groups. The FmKPy-TNF CT ambidextrous gel retains the fibrous nature; however, the size of the fibers changed. In FmKPy-TNF CT gels, TNF is intercalated between pyrene moieties in the self-assembled structure as confirmed by fluorescence quenching and powder X-ray diffraction. The FmKPy ambidextrous gel exhibits significant properties such as low minimum gelation concentration (MGC), thixotropic nature, pH stimuli response, and high thermal stability. Upon the addition of TNF, the FmKPy-TNF CT ambidextrous gel maintains all these properties except MGC which increased for FmKPy-TNF. Because pyrene-based LMW organogels have been developed widely for many applications while their hydrogels were limited, the current finding of the pyrene-based ambidextrous fluorescent gel with the CT property provides a wide opportunity to use FmKPy as a soft material maker and also for potential applications in fields like surface coating, three-dimensional printing, and so forth. © 2017 American Chemical Society.

Langmuir

A Low-Molecular-Weight Gelator Composed of Pyrene and Fluorene Moieties for Effective Charge Transfer in Supramolecular Ambidextrous Gel

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

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

European Journal of Organic Chemistry

10.1002/ejoc.v2018.24

Chemistry of Materials

General Strategy To Fabricate Strong and Tough Low-Molecular-Weight Gelator-Based Supramolecular Hydrogels with Double Network Structure

ACS Applied Energy Materials

Molecular Design Strategy for a Two-Component Gel Based on a Thermally Activated Delayed Fluorescence Emitter

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

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