A new colorimetric and turn-on fluorescent probe NPC-H2S with a large Stokes shift (227 nm) was designed and synthesized for the detection of hydrogen sulfide (H2S) in environmental, food analysis and biological imaging. NPC-H2S was strategically constructed by employing a new corrole derivate (NPC–OH) as the fluorophore and a benzenesulfonyl group (DNBS) as the identification moiety and fluorescence quencher. NPC-H2S displays high selectivity and sensitivity for H2S over various analytes with fluorescent “off-on” ultra-fast recognition (10 s), a low limit of detection (61 nM), and a naked-eye colorimetric change from green to yellow. Importantly, NPC-H2S has been successfully applied for the detection of H2S in the actual water samples and monitoring the spoilage of food samples such as chicken, beef, pork, fish, cracked egg and full egg, as well as for fluorescent bioimaging of H2S in living cells and zebrafish. 

Development of a colorimetric and turn-on fluorescent probe with large Stokes shift for H2S detection and its multiple applications in environmental, food analysis and biological imaging

Hydrogen sulfide (H2S) is not only a well-established toxic gas but also an important small molecule bioregulator in all kingdoms of life. In contemporary biology, H2S is often classified as a "gasotransmitter," meaning that it is an endogenously produced membrane permeable gas that carries out essential cellular processes. Fluorescent probes for H2S and related reactive sulfur species (RSS) detection provide an important cornerstone for investigating the multifaceted roles of these important small molecules in complex biological systems. A now common approach to develop such tools is to develop "activity-based probes" that couple a specific H2S-mediated chemical reaction to a fluorescent output. This Review covers the different types of such probes and also highlights the chemical mechanisms by which each probe type is activated by specific RSS. Common examples include reduction of oxidized nitrogen motifs, disulfide exchange, electrophilic reactions, metal precipitation, and metal coordination. In addition, we also outline complementary activity-based probes for imaging reductant-labile and sulfane sulfur species, including persulfides and polysulfides. For probes highlighted in this Review, we focus on small molecule systems with demonstrated compatibility in cellular systems or related applications. Building from breadth of reported activity-based strategies and application, we also highlight key unmet challenges and future opportunities for advancing activity-based probes for H2S and related RSS.

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species.

Nanomaterials having superior properties have become one of the major components in development of various products for numerous applications. Two-dimensional (2D) nanomaterials like graphene, clay, silicate, layered double oxide, phosphate, and layered metal oxide have remarkable mechanical, electrical, and thermal properties which covert them lucrative material for packaging, electronics, catalyst, batteries and energy applications. 2D materials are in use in the form of unmodified, hybrids, nanocomposites. Surface modification of 2D materials can reduce agglomeration of particles which can lead to better property and economical product. This manuscript discusses basic structure, properties, applications and shortcomings of selective 2D materials (Clay, Carbon allotropes, MXenes, Silicate and Phosphate, 2D metal oxide, Hexagonal boron nitride, MOF and covalent organic framework). Different surface modification techniques such as covalent modification, noncovalent modification, inorganic compounds based functionalization, click chemistry, Π-Π stacking, incorporation techniques, defect creation technique and structural engineering are discussed in corroboration with recent works. 

Recent advancement of surface modification techniques of 2-D nanomaterials

A new series of nonplanar and unsymmetrically β-functionalized "push-pull" copper corroles, CuTPC(CHO)R7 [R = H, Br, Ph, Me, or 2-thienyl (Th)], were synthesized and characterized to elucidate the effect of β-functionalization and nonplanarity on the photophysical, redox, and nonlinear optical (NLO) properties on the corrole ring. The synthetic route to unsymmetrically β-octasubstituted copper corroles includes bromination of CuTPC(CHO) to get CuTPC(CHO)Br7 in 80% yield, which was further subjected to the Pd-catalyzed Suzuki reaction. CuTPC(CHO)Br7 exhibited a large red shift in the Soret band (Δλmax = 35-40 nm) and both the Q bands (Δλmax = 10-50 nm), as compared to CuTPC and CuTPC(CHO). CuTPC(CHO)Br7 was 510 and 290 mV anodically shifted in the first oxidation and the first reduction compared to CuTPC owing to the strong -I effect of CHO and Br groups. Density functional theory studies revealed that all the β-octasubstituted copper corroles exhibited highly nonplanar saddle-shape conformation of the corrole ring. Very high torsional saddling was observed for CuTPC(CHO)Th7 (79-83°) than that for CuTPC (49-53°), even larger than that for CuTPCBr8 (67-70°). Femtosecond laser-induced third-order NLO studies from these copper corroles showed strong two-photon absorption cross-sections (0.48-6.98 × 104 GM) and self-focusing-type positive nonlinear refraction behavior. The observed structure-dependent two-photon absorption coefficients (β) are in the range of ∼2.7-20.9 × 10-12 m/W, and the n2 values are in the range of ∼0.64-6.45 × 10-18 m2/W. The present results may facilitate a new window for these copper corroles in nonlinear optical devices, femtosecond optical limiters, and many other ultrafast photonic applications.

Ultrafast Dynamics and Strong Two-Photon Absorption Properties of Nonplanar β-Functionalized "Push-Pull" Copper Corroles with a Mixed Substituent Pattern.

A porphyrin based fluorescent chemodosimeter, Psium, which a sulfide-nucleophile reactive ester linker is incorporated between a 2-formylphenyl moiety and a benzyl pyridinium substituted porphyrin fluorophore, has been developed for hydrogen sulfide (H2S) detection. Psium behaved a prominent luminescence “off–on” response to H2S with strong anti-disturbance ability over other potential analytes resulted from the H2S-induced nucleophilic substitution–intramolecular elimination cascade reaction. Systematically spectroscopic studies, NMR/MS/HPLC analysis, and DFT calculation further confirmed the proposed mechanism. Advantages including complete water-solubility, low detection limit (46 nM), high specificity, excellent linear relationship and rapid responding empowered Psium to be utilized in H2S detection in actual samples. CLSM analysis further validated the sensing capability of Psium in living HeLa cells, including the visualization of exogenic-added or endogenic-generated H2S, as well as the localization of mitochondrial H2S. This work could potentially present inspiration and offer insights for exploring of other reactive fluorogenic probes for specific assaying in food or biological specimens. 

Mitochondrial-Targeted Red-Fluorescent Chemodosimeter for Hydrogen Sulfide Signaling and Visualizing

A near-infrared fluorescent probe based on corrole derivative with large Stokes shift for detection of hydrogen sulfide in water and living cells

Three novel corroles, 5,15-bis(phenyl)-10-(3-methoxy-4-hydroxylphenyl)- corrole PC, 5,15-bis(naphthyl)-10-(3-methoxy-4-hydroxylphenyl)-corrole NAPC and 5,15-bis(pyrenyl)-10-(3-methoxy-4-hydroxylphenyl)-corrole PYPC, were designed and synthesized. Their graphene oxide (GO) nanohybrids, PC-GO, NAPC-GO and PYPC-GO, were prepared by a covalent functionalization method and characterized by various spectroscopic techniques. The third order nonlinear optical (NLO) behavior of the corroles and their corresponding nanohybrids was investigated using open aperture Z-scan technique at 532 nm with 4 ns laser pulses. The nanohybrids showed enhanced NLO properties in comparison to the corresponding corroles. In addition, the NLO properties of nanohybrids increase in the order of NAPC-GO < PC-GO < PYPC-GO, while the corrole molecules exhibit NLO performance in the same order of NAPC < PC < PYPC, implying the NLO response originating from the corrole moiety play a more important role in the NLO properties of the nanohybrids than that arising from the photo-induced electron or energy transfer process between GO and corrole molecules. Importantly, at same transmission intensity, all the corroles showed typical nonlinear reverse saturation absorption (RSA) behavior, while all the nanohybrids exhibited a flip over behavior from saturation absorption (SA) to RSA. The different NLO response between the corrole molecules and their nanohybrids implies their promising applications as NLO materials. 

Preparation and third order nonlinear optical properties of corrole functionalized GO nanohybrids

Broadly, the industrial applications of hydrazine cause environmental pollution and damage to living organisms because of the high toxicity of hydrazine. Therefore, monitoring hydrazine in the environmental system is of great significance to human health. Here, a new fluorescent probe PC-N2 H4 based on corrole dye was developed for the detection of hydrazine that had excellent specificity, low limit of detection (LOD: 88 nM), and a wide pH range (6-12). Upon addition of hydrazine into the probe solution, the strong red fluorescence was 'turned on' centred at 653 nm with a 127-fold fluorescence intensity enhancement. The detection mechanism was proved using ESI-MS, 1 H NMR, and density functional theoretical calculations. Importantly, the probe was utilized to fabricate a ready-to-use test strip to realize the visual inspection of hydrazine. Furthermore, PC-N2 H4 was successfully applied for practical detection of hydrazine in water samples with satisfactory recoveries ranging from 96.2% to 105.0%, and indicating that the designed PC-N2 H4 is highly promising for hydrazine detection in an aqueous environment. Considering the diverse toxicological functions of hydrazine, PC-N2 H4 was also successfully used to image exogenous hydrazine in HeLa cells and zebrafish. 

Fluorescent detection of hydrazine in an aqueous environment by a corrole derivative.

A Benzenesulfonyl Substituted Corrole-Based Fluorescent Probe for Hydrazine Detection and its Applications

Synthesis and applications of a corrole-based dual-responsive fluorescent probe for separate detection of hydrazine and hydrogen sulfide.

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