Photophysical Properties of Luminescent Zinc(II)‒Pyridinyloxadiazole Complexes and their Glassy Self‐Assembly Networks

Panunzi, Barbara; Concilio, Simona; Diana, Rosita; Shikler, Rafi; Nabha, Shiran; Piotto, Stefano; Sessa, Lucia; Tuzi, Angela; Caruso, Ugo

doi:10.1002/ejic.201800344

Cited by 34 publications

(24 citation statements)

References 46 publications

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“…On the other hand, fluorescence must be guaranteed by a suited emissive core. Heterocyclic molecules [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21], as one of the most important classes of compounds, can play the role of fluorogenic moiety. At present, one of the major problems encountered in optimizing optical sensors is achieving the right balance between the presence of the fluorogenic unit (soluble in organic solvents) and the water solubility.…”

Section: Introductionmentioning

confidence: 99%

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

et al. 2020

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A new 5-(4-((2-(benzothiazole-2-carbonyl)hydrazono)methyl)-3-hydroxyphenoxy)-N,N,N-trimethylpentan-1-aminium bromide (BTABr) fluorescent and colorimetric pH probe was easily synthesized by the condensation reaction of benzothiazole-2-carbohydrazide with 5-(4-formyl-3-hydroxyphenoxy)-N,N,N-trimethylpentan-1-aminium bromide. The benzothiazole moiety provided the emissive part of the molecule and the charged trimethyl amino group guaranteed outstanding solubility in water, for an organic molecule. pH titration experiments indicated that the probe is useful for monitoring acidic and alkaline solutions, turning reversibly in color/fluorescence just at a neutral pH value. Naked-eye colorimetric response was observed both in solution and in the solid state. In addition, the probe showed high stability and selectivity and large Stokes shifts. Because of these features, BTABr can potentially work as an on-off real-time pH sensor for intracellular pH imaging. The crystal structure of BTABr examined by single-crystal analysis showed a planar geometry of the molecule and confirmed the presence of a molecular stacking between molecules joined in a complex tridimensional hydrogen bonding pattern.

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Section: Introductionmentioning

confidence: 99%

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

et al. 2020

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“…The intramolecular hydrogen-bond interactions in the half-salen moieties cause the excited-state intramolecular proton-transfer (ESIPT) [60,61] known to lead to emission in solution [46,59,[61][62][63][64][65][66]. The same effect is known to occur in the solid state [12,67] if the intramolecular H-bond produce hindrance to the torsion of sterically encumbered parts of the molecule [57,68,69].…”

Section: Resultsmentioning

confidence: 99%

“…Due to the excellent semiconducting properties [41,42], benzodifuran scaffolds are used as nonlinear optical materials [43], for dye sensitized solar cells [44] and in organic solar cell and transistors. Finally, as electron-rich building blocks they have a potential in the constructing of photoluminescent materials [45][46][47] Herein, we developed a new benzodifuran derivative from 2,6-diamino-4-(4-nitrophenyl) benzo [1,2-b:4,5-b']difuran-3,7-dicarboxylate [40] (BDF moiety in Scheme 1). Keeping in mind the ability of nitrophenyl ring to twist respect to BDF plane in similar molecules [43], herein, we designed a new T-shaped twisted molecule.…”

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A Novel DR/NIR T-Shaped AIEgen: Synthesis and X-Ray Crystal Structure Study

et al. 2020

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We developed a new benzodifuran derivative as the condensation product between 2,6-diamino -4-(4-nitrophenyl)benzo [1,2-b:4,5-b']difuran-3,7-dicarboxylate and 3-hydroxy-2-naphthaldehyde. The intramolecular hydrogen-bond interactions in the terminal half-salen moieties produce a sterically encumbered highly conjugated main plane and a D-A-D (donor-acceptor-donor) T-shaped structure. The novel AIEgen (aggregation-induced enhanced emission generator) fulfils the requirement of RIR (restriction of intramolecular rotation) molecules. DR/NIR (deep red/near infrared) emission was recorded in solution and in the solid state, with a noteworthy photoluminescence quantum yield recorded on the neat crystals which undergo some mechanochromism. The crystal structure study of the probe from data collected at a synchrotron X-ray source shows a main aromatic plane π-stacked in a columnar arrangement.Crystals 2020, 10, 269 2 of 15 law [20][21][22] the intrinsic low band-gap of such DR/NIR emitters makes them especially vulnerable to the ACQ effect [23] due to higher vibrionic coupling between the ground and excited states. Therefore, most of the AIEgens reported emit blue and green lights. Although they are highly sought after for red OLEDs (Organic Light Emitting Diodes), night-vision devices, secured displays, optical waveguides and in the wide field of bio and chemo-sensing [24][25][26][27][28], there are fewer efficient DR/NIR (deep red/near infrared) materials. Of particular interest are AIE fluorophores with intense emission at DR/NIR region owing to their deep tissue penetration, photo-stability and minimum interference in living systems [25,29,30]. Their applications are closely related to cell imaging and DNA and protein sensing [31][32][33].Novel molecular construction of DR/NIR AIEgens can be achieved with electron donor (D) and electron acceptor (A) blocks connected through π-conjugated frameworks. The most fundamental phenomenon governing the spectroscopic properties is the intramolecular charge transfer (ICT) process from the donor to the acceptor in the excited state [34][35][36]. Intercrossed excited state between the low-lying local exciton (LE) and charge transfer (CT) exciton results from the D-A interaction. Obviously, the molecular geometry is crucial for the process.Benzodifuran derivatives have drawn attention for a wide range of biological and pharmacological applications, including antimicrobial, antiviral, analgesic and antitumor [37][38][39][40] activity. This class of heterocyclic compounds are also employed in dyes industry as pigments and in different fields of optoelectronics and photonics. Due to the excellent semiconducting properties [41,42], benzodifuran scaffolds are used as nonlinear optical materials [43], for dye sensitized solar cells [44] and in organic solar cell and transistors. Finally, as electron-rich building blocks they have a potential in the constructing of photoluminescent materials [45][46][47] Herein, we developed a new benzodifuran derivative from 2,6-diamino-4-(4-nitrophenyl) ...

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“…The benzoyl bulky groups of the dialdehydes A12G and AV12 were added to restrict chain motion and reduce detrimental intermolecular interactions [14,37,38].…”

Section: Compoundmentioning

confidence: 99%

Novel Solid-State Emissive Polymers and Polymeric Blends from a T-Shaped Benzodifuran Scaffold: A Comparative Study

et al. 2020

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Two novel polyimines were synthesized from a benzodifuran based diamino monomer and two dialdehydes bearing bulky groups and a flexible spacer. The polymers display tuned luminescence performance according to the presence of half-salen groups. The effect of the intramolecular bond on the emission properties were examined. Two model compounds, replicating the same emissive Schiff base cores, were synthetized. From the models, dye-doped blends in the fluorophore/matrix ratio, resembling the polymers, were produced. Amorphous thin films of the covalent polymers and the polymeric blends were obtained by spin-coating technique. The Photoluminescent (PL) response of the different macromolecular systems were qualitatively and quantitatively examined and compared.

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Photophysical Properties of Luminescent Zinc(II)‒Pyridinyloxadiazole Complexes and their Glassy Self‐Assembly Networks

Cited by 34 publications

References 46 publications

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

A Novel DR/NIR T-Shaped AIEgen: Synthesis and X-Ray Crystal Structure Study

Novel Solid-State Emissive Polymers and Polymeric Blends from a T-Shaped Benzodifuran Scaffold: A Comparative Study

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