Cyanostilben-based derivatives: mechanical stimuli-responsive luminophors with aggregation-induced emission enhancement

Zhang, Yujian; Sun, Jingwei; Bian, Gaofeng; Chen, Yiyi; Ouyang, Mi; Hu, Bin; Zhang, Cheng

doi:10.1039/c2pp05404c

Cited by 86 publications

(55 citation statements)

References 47 publications

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“…64 However, when water fraction was increased from 60% to 90%, emission maximum was blue-shifted due to elimination of solvent polarity effect in the aggregates. 68 This blue shift emission upon aggregation is common behavior in all the three derivatives ( Table 3). The fluorescence studies of derivative 1 showed small enhancement in emission intensity with increase in water fraction upto 50% which is due to better stabilization of its charge transfer state in more polar solvents (vide supra).…”

Section: Acq To Aiementioning

confidence: 68%

Carbazole-functionalized polyphenylene-decorated solid state emissive D–A–D molecules: reduced donor–acceptor interaction and enhanced emission in the solid state

Singh

Bhalla

2015

Phys. Chem. Chem. Phys.

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A new series of D-A-D molecules (1-3) with carbazole as a donor and 2,5-diaryl-1,3,4-oxadiazole, dibenzothiophene-S,S-dioxide and benzo[1,2,5]thiadiazole as acceptors have been synthesized. Polyphenylene dendrons have also been incorporated to prevent the face to face π-π stacking in aggregates. Unlike traditional D-A systems, which show ACQ problems and large red shifts in the solid state, these derivatives (1-3) exhibit good solid state luminescence behavior without undergoing a red shift or fluorescence quenching. The present results indicate that just the combination of a donor-acceptor system with bulkier dendrons is not enough to generate efficient solid state emissions but the prevention of co-facial interaction between donors and acceptors in aggregates is more important. In the case of derivative 3, restriction of complete molecular planarization and steric hindrance near the acceptor can effectively prevent intermolecular donor-acceptor interactions, thus leading to enhanced emission in aggregates. While in the case of derivative 1, a sterically unhindered acceptor is easily approached by a donor due to close molecular packing in aggregates forming weakly luminescent species.

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Section: Acq To Aiementioning

confidence: 68%

Carbazole-functionalized polyphenylene-decorated solid state emissive D–A–D molecules: reduced donor–acceptor interaction and enhanced emission in the solid state

Singh

Bhalla

2015

Phys. Chem. Chem. Phys.

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“…In addition, the bulky and nonplanar shape of the TPA and DPA facilitate phase transformations that usually occur in MCF materials. Zhang and co‐workers has explored some basic structures, among which only α‐CN‐TPA ( Figure A) the cyano group near the TPA unit is able to switch from almost no fluorescence in the blue region to sky‐blue as consequence of crystal–crystal transitions. The isomeric molecule ( β‐CN‐TPA ) did not show MCF properties on grinding as the original solid was not disturbed.…”

Section: Solid‐state: Polycrystalline Powders Single Crystals and Tmentioning

confidence: 99%

Self‐Assembled α‐Cyanostilbenes for Advanced Functional Materials

2017

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In the specific context of condensed media, the significant and increasing recent interest in the α-cyanostilbene (CS) motif [ArCHC(CN)Ar] is relevant. These compounds have shown remarkable optical features in addition to interesting electrical properties, and hence they are recognized as very suitable and versatile options for the development of functional materials. This progress report is focused on current and future use of CS structures and molecular assemblies with the aim of exploring and developing for the next generations of functional materials. A critical selection of illustrative materials that contain the CS motif, including relevant subfamilies such as the dicyanodistyrylbenzene and 2,3,3-triphenylacrylonitrile shows how, driven by the self-assembly of CS blocks, a variety of properties, effects, and possibilities for practical applications can be offered to the scientific community, through different rational routes for the elaboration of advanced materials. A survey is provided on the research efforts directed toward promoting the self-assembly of the solid state (polycrystalline solids, thin films, and single crystals), liquid crystals, nanostructures, and gels with multistimuli responsiveness, and applications for sensors, organic light-emitting diodes, organic field effect transistors, organic lasers, solar cells, or bioimaging purposes.

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“…In addition, we report reversible fluorescence switching of some of the butadiynyl derivatives in the solid state by external heating and rubbing stimuli. Although there are reports on stimuli responsive fluorophores, [42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57] reports pertaining to a single fluorophore are still limited. Further, the potential of conjugated 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 diacetylenes as stimuli responsive fluorophores in the solid powder has not been looked at yet in the literature.…”

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confidence: 99%

Contrasting Solid-State Fluorescence of Diynes with Small and Large Aryl Substituents: Crystal Packing Dependence and Stimuli-Responsive Fluorescence Switching

2015

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There has been a significant current interest in solid state luminescence of organic molecules and their stimuli responsive fluorescence switching behavior. Although small organic derivatives with olefinic, acetylenic, phenylenevinylenic, phenyleneethynylenic spacers are widely documented as solid state emitters in the literature, the solid state photophysics of organic derivatives with "butadiyne" spacer still remains unexplored. We provide detailed investigation on the solid state fluorescence properties of a series of butadiynyl fluorophores. Replacement of a phenyl ring, which is at periphery of the butadiyne bridge, with a large moiety such as pyrenyl group furnishes contrasting emissions in the solid state. While the butadiyne bridged phenyl derivatives show a blue shift of emission maxima in the solid powder with respect to monomer spectra in solution state, the butadiyne bridged pyrenyl derivatives exhibit a red shift in the solid state. The blue shift of the emission maxima of the butadiyne bridged phenyl derivatives in the solid powder is attributed to allowed excitonic transition in aggregates with nearly parallel transition dipoles. On the other hand, formation of pyrenyl excimer accounts for the red shift of the butadiyne bridged pyrenyl derivatives in the solid powder. In addition to that, the solid state fluorescence of the pyrenyl analogues is reversibly switched between two aggregate forms through external heating and rubbing stimuli.

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Cyanostilben-based derivatives: mechanical stimuli-responsive luminophors with aggregation-induced emission enhancement

Cited by 86 publications

References 47 publications

Carbazole-functionalized polyphenylene-decorated solid state emissive D–A–D molecules: reduced donor–acceptor interaction and enhanced emission in the solid state

Carbazole-functionalized polyphenylene-decorated solid state emissive D–A–D molecules: reduced donor–acceptor interaction and enhanced emission in the solid state

Self‐Assembled α‐Cyanostilbenes for Advanced Functional Materials

Contrasting Solid-State Fluorescence of Diynes with Small and Large Aryl Substituents: Crystal Packing Dependence and Stimuli-Responsive Fluorescence Switching

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