Tuneable solid-state emitters based on benzimidazole derivatives: Aggregation induced red emission and mechanochromism of D-π-A fluorophores

Horak, Ema; Robić, Marko; Šimanović, Aleksandra; Mandić, Vilko; Vianello, Robert; Hranjec, Marijana; Steinberg, Ivana Murković

doi:10.1016/j.dyepig.2018.10.069

Cited by 52 publications

(31 citation statements)

References 53 publications

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“…An AIE phenomenon is especially exploited in solid-state, where the concentration effect commonly causes fluorescence quenching. Having in mind that fluorophores emitting in the solid states are extremely rare, especially red ones, benzimidazole-based AIE molecular systems show a great prospect for future applications of pristine powder samples or crystals as solid-state sensors and 'smart' materials [61][62][63][64][65].…”

Section: Aggregation-induced Emittersmentioning

confidence: 99%

“…Besides optical sensing, paper-based materials coated with functional benzimidazole derivatives are also presented as 'smart' , stimuli responsive materials with potential applications in security, optoelectronic or fluorescent imaging [62]. Simple sensing substrates such as paper and textile materials are perfectly suited…”

Section: Other Benzimidazole-based Materials For Optical Sensingmentioning

confidence: 99%

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Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Horak¹,

Vianello²,

Steinberg³

2019

Chemistry and Applications of Benzimidazole and Its Derivatives

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Benzimidazole derivatives are well-known biologically active substances, and therefore, they are mostly synthesised for therapeutic purposes. However, such heteroaromatic molecular systems own structure-related properties that enable a variety of applications, especially in optical science. Multifunctionality of the benzimidazole unit, such as electron accepting ability, π-bridging, chromogenic pH sensitivity/switching and metal-ion chelating properties, makes it an exceptional structural candidate for the design of optical chemical sensors and functional materials. Development of smart molecular sensors and novel (nano)materials is the emerging trend observed in materials and optical sensing science in general, in which the benzimidazole molecular systems strongly contribute and participate. In this chapter, we summarised recent advances in optical sensing (nano)materials that incorporate the benzimidazole structural moiety. Solid-state optical sensing systems, including self-assembled molecular materials based on benzimidazoles, are reviewed and discussed. In addition, immobilisation of benzimidazole derivatives onto or into various substrates and matrices, such as organic and inorganic polymers, bulk membranes and nanoparticles, utilising different chemical and physical methods, is presented and analysed.

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Section: Aggregation-induced Emittersmentioning

confidence: 99%

Section: Other Benzimidazole-based Materials For Optical Sensingmentioning

confidence: 99%

Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Horak¹,

Vianello²,

Steinberg³

2019

Chemistry and Applications of Benzimidazole and Its Derivatives

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“…[23,24] When N1 and C2 positions of PI are modified with ab enzene ring, one of the most commona nd typical derivatives, namely 1,2diphenylphenanthroimidazole (PPI, Scheme 1) is obtained. [25,26] PPI is an itrogen-containing heterocyclic conjugate group with ar igid planar conjugated structure having excellent properties, such as high fluorescenceq uantum yield and wide light absorption, whichm ake it very attractive for employment as a buildingb lock for the preparation of blue emitters. [27][28][29][30] PPI can effectively reducet he energy loss of nonradiative transition and exhibits good thermals tability.…”

Section: Introductionmentioning

confidence: 99%

Disentangling Multiple Effects on Excited‐State Intramolecular Charge Transfer among Asymmetrical Tripartite PPI‐TPA/PCz Triads

Yang

Cao

Islam

et al. 2020

Chemistry A European J

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By utilizing the bipolarity of 1,2-diphenylphenanthroimidazole (PPI), two types of asymmetricalt ripartite triads (PPI-TPAa nd PPI-PCz) were designed with triphenylamine (TPA) and 9-phenylcarbazole (PCz). These triads are deep-blue luminescentm aterials with ah igh fluorescence quantumy ield of nearly 100 %. To trace the photophysical behaviors of these triads, their excited-state evolutionc hannels and interchromophoric interactions were investigated by ultrafast time-resolved transient absorptiona nd excitedstate theoretical calculations.T he resultss uggest that the electronic nature, asymmetricalt ripartite structure, and electron-hole distance of these triads, as wella ss olvent polarity, determine the lifetimeo fi ntramolecular charget ransfer (ICT). Interestingly,P PI-PCz triads show anti-KashaI CT,a nd the charge-transfer direction among the triads is adjustable. For the PPI-TPA triad, the electron is transferred from TPAt o PPI, whereas fort he PPI-PCzt riad the electron is pushed from PPI to PCz. Exploration of the excited-state ICT in these triads mayp ave the wayt od esign better luminescent materials in the future.

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“…1 9-((4-((4-([2,2':6',2''-terpyridin]-4'-yl)phenyl)ethynyl) phenyl)ethynyl)-9H-carbazole (6). In a Schlenk flask, Pd(PPh 3 ) 2 Cl 2 (40.3 mg, 0.06 mmol) and CuI (11.0 mg, 0.06 mmol) were added to a solution of ((4-bromophenyl)ethynyl)trimethylsilane (17 (19) (93.2 mg, 0.30 mmol)in anhydrous THF (7 mL). The reaction mixture was purged with nitrogen and heated at 70°C for 5 days.…”

Section: Methodsmentioning

confidence: 99%

“…[15,16] Among many options for the design of organic πconjugated molecules, the combination of an electron donor (D) and a related acceptor (A) is particularly interesting, as it affords "push-pull" systems, which are well suited for organic electronics, semiconductors and photovoltaics. [17] The A/D subunits can be covalently connected through different rigid and conjugated systems, so as to prepare D-π-A architectures [18][19][20][21][22][23] which may show a characteristic photophysical behaviour, in particular charge-transfer absorption (and possibly emission) bands, typically red-shifted compared to spectral features arising from local excited states centred on the individual subunits. [24] Electron-rich moieties containing fused aromatic rings can exhibit high carrier mobilities, enhanced fluorescence and reduced band gaps.…”

Section: Introductionmentioning

confidence: 99%

Carbazole‐Terpyridine Donor‐Acceptor Dyads with Rigid π‐Conjugated Bridges

et al. 2019

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A series of molecules in which 9H‐carbazole (electron donor, D) and 2,2′:6′,2′′‐terpyridine (electron acceptor, A) are connected through rigid π‐conjugated bridges (D‐π‐A systems) have been synthesized and their photophysical properties examined in detail, with the support of DFT calculations. The bridges are made of different sequences of ethynylene, phenylene, and anthracene groups. The synthetic strategies involve condensation of 2‐acetylpyridine with the aromatic aldehyde moiety on different functionalized π‐conjugated bridges and couplings with carbazole derivatives. The system incorporating anthracene in the bridge shows the typical absorption and emission fingerprints of this polycyclic hydrocarbon. The other systems have HOMOs and LUMOs centred, respectively, over the carbazole and the bridge and exhibit solvatochromic charge‐transfer (CT) luminescence with high photoluminescence yield up to 70 %, except when an ethynylene unit is directly attached to the carbazole ring, due to a trans‐bent non‐emissive π–σ* excited state.

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Tuneable solid-state emitters based on benzimidazole derivatives: Aggregation induced red emission and mechanochromism of D-π-A fluorophores

Cited by 52 publications

References 53 publications

Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Disentangling Multiple Effects on Excited‐State Intramolecular Charge Transfer among Asymmetrical Tripartite PPI‐TPA/PCz Triads

Carbazole‐Terpyridine Donor‐Acceptor Dyads with Rigid π‐Conjugated Bridges

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