Solid-State Highly Efficient DR Mono and Poly-dicyano-phenylenevinylene Fluorophores

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

doi:10.3390/molecules23071505

Cited by 28 publications

(25 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All photophysical measurements were performed in water solution or waterethanol (8:2), the addition of ethanol slightly increasing emission intensity. The fluorescence quantum yield was measured in water for the deprotonated form D at pH = 11.0 by relative methods using quinine sulfate (QS) as standard (0.546 in H2SO4 1 N, excited at 365 nm) according to [32][33][34]. The value of 6.20% is comparable to that reported for water-soluble pH probes [35,36].…”

Section: Characterization and Sensing Ability Of Btabrmentioning

confidence: 71%

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

et al. 2020

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: Characterization and Sensing Ability Of Btabrmentioning

confidence: 71%

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…DR/NIR solid-state emitters are intrinsically narrow band gap materials typically with π-conjugated planar molecules especially vulnerable to solid-state emission quenching due to the strong π-π overlap favoring aggregation [ 21 ]. As an alternative, π-conjugated backbones such as phenylenevinylene (PV) skeleton, with strong donor (D) and acceptor (A) functionalities can show interesting DR/NIR emission in the solid state [ 22 , 23 , 24 ]. In most cases, the efficient red emission arises from an intramolecular charge-transfer (ICT) state and bulky side groups, such as cyano, can impede excessive excitonic and electronic coupling.…”

Section: Introductionmentioning

confidence: 99%

AIE/ACQ Effects in Two DR/NIR Emitters: A Structural and DFT Comparative Analysis

et al. 2018

Self Cite

View full text Add to dashboard Cite

The effects of aggregation-induced emission (AIE) and of aggregation caused quenching (ACQ) were observed and discussed on two solid materials based on a phenylenevinylene (PV) and a dicyano-PV structure. The brightest emitter in solid films shows a high fluorescence quantum yield in the deep red/near IR (DR/NIR) region (75%). The spectroscopic properties of the two crystalline solids have been described and compared in terms of crystallographic data and time dependent DFT analysis. The influence of the cyano-substituents on AIE/ACQ mechanism activation was discussed.

show abstract

“…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%

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

et al. 2020

Self Cite

View full text Add to dashboard Cite

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) ...

show abstract

Solid-State Highly Efficient DR Mono and Poly-dicyano-phenylenevinylene Fluorophores

Cited by 28 publications

References 38 publications

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

AIE/ACQ Effects in Two DR/NIR Emitters: A Structural and DFT Comparative Analysis

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

Contact Info

Product

Resources

About