Fabiano Severo Rodembusch

Fabiano Severo Rodembusch
Universidade Federal do Rio Grande do Sul | UFRGS · Departamento de Química Orgânica (DQO)

Doctor of Philosophy
Associate Professor / Photochemistry / Organic Chemistry and Materials Science Researcher (Chico's Father)

About

163
Publications
14,512
Reads
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2,671
Citations
Citations since 2016
95 Research Items
2014 Citations
20162017201820192020202120220100200300400
20162017201820192020202120220100200300400
20162017201820192020202120220100200300400
20162017201820192020202120220100200300400
Introduction
Organic photochemistry, photoactive organic-inorganic hybrid materials and optical sensing
Additional affiliations
March 2007 - present
Universidade Federal do Rio Grande do Sul
Position
  • Professor
Education
December 2013 - April 2014
University of Miami
Field of study
  • Supramolecular Photochemistry
November 2005 - November 2006
Université de Montpellier 2, France
Field of study
  • Hybrid materials and sol-gel
March 2001 - February 2005
Universidade Federal do Rio Grande do Sul
Field of study
  • Organic Chemistry

Publications

Publications (163)
Article
This study describes the synthesis of new pyromellitic diimide (PMDI) derivatives obtained in good yields from the reaction between pyromellitic dianhydride and aminobenzazoles reactive to proton-transfer in the excited state (ESIPT). In this investigation, a non-ESIPT PMDI was also prepared for comparison. These compounds presented absorption maxi...
Article
The present work describes the synthesis of three classes of mono-silylated benzothiadiazole and their application in obtaining organic-inorganic fluorescent hybrid materials. The mono-silylated compounds were obtained through a Pd-catalyzed Sonogashira coupling reaction with silicon-functionalized alkynes (25–61% yield). One of the silylated produ...
Article
Fluorescent and colorimetric sensors are important tools for investigating the chemical compositions of different matrices, including foods, environmental samples, and water. The high sensitivity, low interference, and low detection limits of these sensors have inspired scientists to investigate this class of sensing molecules for ion and molecule...
Article
Herein, we report the synthesis of bis-silylated 2,1,3-benzothiadiazole derivatives and their use in the preparation of photoactive organic-inorganic hybrid materials with extremely low fluorophore/tetraethylorthosilicate molar ratios. The organic compounds were synthesized in good to excellent yields (55%-94%) using Pd-catalyzed Sonogashira cross-...
Article
This study describes the synthesis, photophysical characterization, and TD-DFT calculation of a series of benzothiazole-based styryl fluorophores (F1-F5) harboring a D-π-A structure. The compounds were obtained through a simple and efficient synthetic route using low-cost starting materials. The investigation and analysis of their photophysical pro...
Article
This study describes the synthesis and characterization of novel π-conjugated compounds based on 1,3-diynes containing an alkylated tetrazole moiety. Optical properties were characterized by UV–Vis absorption and fluorescence emission spectrophotometry, showing absorption in the ultraviolet region with a molar absorption coefficient of approximatel...
Article
This review summarizes diverse synthetic methodologies to prepare a wide range of heptamethine cyanine dyes, including symmetrical, unsymmetrical, and meso‐substituted derivatives, and their photophysical properties and use. Their sensing applications are also discussed, considering the nature of their electronic structures and photophysical proper...
Article
In this article, the binding affinity of 1,4-dihydropyridine-based hexahydroquinoline-3-carboxylates with bovine serum albumin (BSA) was studied by electronic spectroscopies, quantum calculations, and molecular docking. These compounds were obtained by the one-pot microwave-assisted method via a modified Hantzsch reaction. The photophysical charact...
Presentation
We presented a lamellar K4Nb6O17.xH2O hexaniobate (KNbO) decorated with sputtered Cu, Ag, and Au nanoparticles (MNPs) for photocatalytic hydrogen production from water/methanol solutions and describe the effect of embedded 1-butyl-3-methyl-imidazolium bis((trifluoromethyl)sulfonyl) amide ionic liquid (IL) over catalyst performance. At chosen sputte...
Article
This review summarizes diverse synthetic methodologies to prepare a wide range of heptamethine cyanine dyes, including symmetrical, unsymmetrical, and meso‐substituted derivatives, and their photophysical properties and uses. Their sensing applications are also discussed, considering the nature of their electronic structures and photophysical prope...
Article
Herein, we report a photocatalytic device based on gold nanoparticles (AuNPs)/titanium dioxide (TiO2) nanomaterial coated with an ionic liquid (IL) as a very active, stable, and versatile system for hydrogen evolution reactions (HERs) via aqueous methanol photo reforming (MPR) and water splitting (WSR). The devices prepared by magnetron sputtering...
Article
Full-text available
In this study, the interactions of ESIPT fluorescent lipophile-based benzazoles with bovine serum albumin (BSA) were studied and their binding affinity was evaluated. In phosphate-buffered saline (PBS) solution these compounds produce absorption maxima in the UV region and a main fluorescence emission with a large Stokes shift in the blue–green reg...
Article
This work reports the synthesis of four homomolecular bis(n)-Lophines dyads achieved by a one-pot four component reaction. The dyads show absorption maxima below 300 nm and present intense fluorescence emission, with large Stokes shift, around 380 nm. Intercalation phenomenon and hydrophobic forces can be predicted for dyads, according to the resul...
Article
This review summarizes several aspects of type II photoactive organic-inorganic hybrid materials prepared from silylated fluorophores, including their photophysical properties and uses. In this sense, several examples are presented and discussed taking the nature of the silyl derivative into account. Applications as latent fingerprints detection, c...
Article
Diverse structural frameworks are found in natural compounds and are well known for their chemical and biological properties; such compounds include the imidazoles and oxazoles. Researchers worldwide are continually working on the development of methods for synthesizing new molecules bearing these basic moiety and evaluating their properties and ap...
Article
The development of biodegradable curative systems containing antibacterial drug are fundamental for the promotion of therapeutic actions, reducing the infections caused by microorganisms and being able to substitute conventional dressings which are not biodegradable polymers in their composition. Meeting those needs, poly (butylene adipate‐co‐terep...
Article
Full-text available
In this work, the role of deoxycholic acid (DCA) as a coadsorbent was investigated in the sensitization of mesoporous TiO2 layers (host) with symmetrical carboxy heptamethine cyanine dyes (guest). Different approaches have been tested, aimed at reducing the H-aggregation and minimizing the competition between cyanine molecules and DCA for active si...
Article
ZnO nanoparticles were successfully synthesized using cassava starch (tapioca) as a chelating agent. X-ray diffraction (XRD) and Fourier transform infrared (FTIR) analyses revealed that the synthesized nanoparticles were in the form of ZnO with no impurities present. The estimated average crystallite size, determined from Rietveld refined XRD patte...
Article
Benzothiazole derivatives were used as models to study the excited-state intramolecular proton transfer (ESIPT) in an experimental and theoretical point of view. The experimental electronic and vibrational results were compared with a comprehensive selection of state-of-the-art computational methods in a workflow approach. These latter were perform...
Article
Zn(II) coordination compounds with asymmetric salicylidene ligands in PFO composites were used for all-solution-processable white organic light-emitting diodes (WOLEDs) purposes. These Zn(II) complexes were strategically synthesized to optimize their electronic structures, starting from the widespread known salophen core. Vertical excitation energi...
Article
Multivariate Curve Resolution with Alternating Least Squares (MCR-ALS) was for the first time successfully used to evaluate an intricate photophysical behavior, where deprotonation on the electronic ground state (S0), intra and intermolecular proton transfer processes (ESPT and ESIPT) on the electronic excited state (S1) can simultaneously be prese...
Presentation
Here we report the effect of ionic liquids over sputtered Au nanoparticles on TiO2 for hydrogen production in aqueous methanol and using monochromatic UV-A-LED light strips to activate the surface. Different sputtering conditions afforded to AuTi1-7 catalytic systems that were subsequently embedded with ionic liquids [BMIm.OAc](IL1); [BMIm.NTf2](IL...
Article
Herein, we describe the syntheses of symmetric and asymmetric benzothiadiazole (BTD)-based fluorophores via the Sonogashira coupling reaction, using 4,7-dibromobenzothiadiazole as the central core and propargyl carbazole and/or propargyl diphenylamine as the side groups. The synthesized fluorophores exhibited absorption bands in the ultraviolet reg...
Article
This work describes the synthesis of new fluorophores based on non-symmetric 4,7-dibromobenzo[c][1,2,5]thiadiazole derivatives with benzene ethynyl tetrazole and propargyl carbazole as terminal groups. The new compounds were obtained using the Sonogashira cross-coupling reaction and produced good yields. The benzothiadiazole derivatives presented a...
Article
A series of new hybrid fluorescent Biginelli compounds, including a Monastrol derivative were designed and synthesized with good yields. The photophysical studies revealed dual fluorescence emission, attributed to excited enol forms (E*) and tautomeric (K*) species, respectively, due to the ESIPT mechanism. The cytotoxic activity of all compounds w...
Article
This study presents a low-cost method for obtaining nanometric zinc oxide (ZnO) using a cassava starch (Tapioca)-assisted by sol-gel route. In this procedure, ZnO nanopowders (~20 nm and 59 nm according to XRD) were obtained after 2 h of calcination at 500oC. The cassava starch played a fundamental role during the sol-gel synthesis allowing the obt...
Article
This study presents the synthesis in good overall yields of oxazolidine-based ionic compounds obtained from protected l-serine followed by an esterification reaction with bromoalcohols and a reaction with 1-methylimidazole in acetonitrile under reflux. These compounds present in ethanol solution an absorption maxima located around 210 nm, resulting...
Article
New isomeric tetra-cationic porphyrins containing peripheral [Pd(bpy)Cl]+ units attached at pyridyl substituents were synthetized and fully characterized. The porphyrins present an intense Soret band located in the blue spectral region and additional four weaker red-shifted Q bands in the visible spectral region (about 500-700 nm). The obtained Str...
Article
A series of 1,3-benzoselenazole derivatives were prepared with different substituents by complementary methodologies starting from aldehydes or carboxylic acids, using sodium metabisulfite and tributylphosphine, respectively, according to the substituent pattern. The photophysical behaviour in solution of the benzoselenazoles was studied using UV–V...
Article
Full-text available
In this study, we synthesized a spiropyran containing an electron-withdrawing carboxyl group in good yield by condensation of an aromatic aldehyde with enamine indole. The spiropyran absorbed at the ultraviolet region with a maximum at approximately 300 nm, demonstrating slight solvatochromism (~3 nm). A fluorescent emission around 360 nm was obser...
Article
Substituted merocyanine dyes were obtained by Knoevenagel condensation between formylated arylbenzothiazole and quaternary 2-alkylbenzothiazoles. The condensations were performed in the presence of sodium methoxide and the products were obtained with excellent yields after simple purification. The merocyanines presented absorption maxima in the ran...
Article
A novel selective fluorescent sensor for Cu²⁺ in solution has been developed by means of chelation enhancement quenching effect (CHEQ). The compound N,N′-bis(salycilidene)-(2-(3′,4′-diaminophenyl)benzothiazole (BTS) is reactive to intramolecular proton transfer on the electronic excited state (ESIPT) presenting fluorescence emission in the blue reg...
Article
Lipophilic 2,1,3-benzothiadiazoles were obtained in a short synthesis with excellent yields by a Sonogashira coupling reaction followed by a 1,3-dipolar cycloaddition reaction with alkyl azides. The obtained compounds presented high solubility in a wide range of solvents with different polarities. The benzothiadiazoles present absorption in the vio...
Article
Herein we report the synthesis of a series of amino acid-derived triazoles by an organocatalytic cycloaddition reaction between azides and carbonyl compounds, catalyzed by a simple amine. These compounds present absorption maxima located in the UV-B ascribed to fully spin and symmetry allowed electronic transitions and a main fluorescence emission...
Article
A series of luminescent aryloxy-benzothiadiazole derivatives with architectures ArO-BTD-Ar’ and ArO-BTD-NAr’ were synthetized. The aim was to achieve a molecular design based on restriction of intramolecular rotation of the ArO- group associated to the presence of bulky aryl or N-aryl groups, which can avoid detrimental π-π stacking and favor radia...
Article
This work presents the synthesis, photophysical characterization, and application of ATRP polymerization initiators to produce photoactive solid-state fluorescent polystyrene-based polymers. These compounds present absorption in the UV region (∼340 nm) and emission in the blue-green regions with large Stokes shift (∼10 000 cm−1) due to a proton tra...
Article
The changes in the ability of three fluorescent derivatives of 2-(2’-hydroxyphenyl)benzothiazole to undergo excited-state intramolecular proton transfer (ESIPT) processes have been correlated with the rheological properties of four amino-polydimethylsiloxanes with different molar masses and containing different amounts of monomer units with amino p...
Article
This work describes the synthesis and photophysical investigation of amino and azido benzazoles. The amino derivatives were obtained by condensation reaction between ortho-substituted anilines and p-aminobenzoic in polyphosphoric acid. The respective azides were synthesized by reaction of diazonium salts from the previously prepared amines with sod...
Article
The effects of the polymeric matrix on the photophysical properties of monomeric dyes reactive to Excited State Intramolecular Proton Transfer (ESIPT) were evaluated by UV–Vis absorption and steady-state and time-resolved emission spectroscopies. A radical polymerization reaction was used to produce new photoactive styrene-based polymeric matrices....
Article
Full-text available
The impact of cerium (Ce) and neodymium (Nd) rare-earth metal doping of TiO2 prepared by the hydrothermal method was investigated to tailor effective photocatalytic degradation of coloured wastewater under UV or visible illumination. The hydrothermal treatment of TiO2 decreased the pHpzc from 6.3 to 3.1–3.8 favouring the affinity for cationic water...
Article
This study presents new Tröger’s bases bearing glycosyl moieties obtained from a copper-catalyzed azide–alkyne cycloaddition reaction. The Tröger’s bases present absorption maxima close to 275 nm related to fully spin and symmetry-allowed electronic transitions. The main fluorescence emission located at 350 nm was observed with no influence on the...
Patent
Full-text available
INPI - Instituto Nacional da Propriedade Industrial Patent application: 05/07/2019
Article
A series of new organochalcogen derivatives of benzimidazo[1,2-a]quinolines were synthesized in moderate to excellent yields and in short reaction times from chalcogen benzimidazoles, in a straightforward synthetic procedure, through transition-metal-free cascade reactions involving a sequential intermolecular aromatic nucleophilic substitution (SN...
Article
A new salicylidene derivative, the N,N′-bis(salicylidene)-(2-(3′,4′-diaminophenyl)benzothiazole (BTS), which exhibits an Excited State Intramolecular Proton Transfer (ESIPT) process was synthesised and successfully used as a guest in poly[9,9-dioctylfluorenyl-2,7-diyl] (PFO) for an all-solution-processed Organic Light-Emitting Diode (OLED). Compare...
Article
This study reports the synthesis of two photoactive molecular hybrids containing Tacrine and pyrimidine moieties achieved by multicomponent reaction. The hybrids 11a and 11b present absorption maxima close to the Tacrine absorption (~320 nm). The hybrids present fluorescence emission around 400 nm, as observed for the separate Tacrine and pyrimidin...
Article
In this article, new fluorescent lipophilic based benzazoles were synthesized from the reaction between photoactive formyl derivatives and aliphatic amines followed by NaBH4 reduction with good yields. The photophysics of the benzazoles were investigated experimentally and theoretically. These compounds present absorption maxima in the UV region (∼...
Article
A series of oxazoline based compounds was obtained via amidation formation from salicylic acid derivatives and benzyl-protected L-threonine with good yields (50–90%). These compounds present absorption in the UV region (∼300 nm) and fluorescence emission spectra show large Stokes shift emission (∼10000 cm ⁻¹ ) in the blue-green region attributed to...
Article
Full-text available
This work presents the synthesis, characterisation and theoretical calculations of compounds that contain electron donor and withdrawing groups connected through a π-conjugated benzazolic structure. The compounds in solution show an absorption maxima in the UV-visible spectrum (380-390 nm) due to spin and symmetry allowed electronic 1ππ* (ε∼10⁴M⁻¹•...
Article
A salicylidene derivative, N,N’-bis(salicylidene)-(2-(3’,4’-diaminophenyl)benzothiazole (BTS), reactive to the Excited State Intramolecular Proton Transfer process (ESIPT), was synthesized and its photophysical properties were evaluated, presenting an emission covering the entire range of the visible spectrum. Due to its broad emission band, BTS wa...
Article
This work describes the synthesis of photoactive proton transfer compounds based on the benzazolic core containing the azide group. The compounds present absorption in the UV region and fluorescence emission in the visible region of the spectra with large Stokes shift due to a phototautomerism in the excited state (ESIPT). The azide location on the...
Article
Nanostructured titanium dioxide with high photocatalytic efficiency was synthesised by the oxidant peroxide method and microwave‐assisted hydrothermal treatment without calcination or doping. The influence of pH during hydrothermal treatment was investigated on the morphology, crystallinity, phase composition, specific surface area, photoluminescen...
Article
This study involves the electrochemical, thermal and photophysical profiling of new pyromellitic diimide (PMDI) derivatives containing alkyl chains of different sizes. The photophysical investigation shows that all compounds exhibited absorption in the UV-B region (∼290 nm). The band-gaps were calculated by onset peak values of around 4.03 eV. The...
Article
Two photoactive molecular hybrids containing both lophine and pyrimidine moieties were synthesized by multicomponent reaction. The compounds present absorption in the UV-region (below 300 nm) and fluorescence emission in the violet region due to the lophine moiety. Experimental evidences indicates that photoinduced electron transfer (PET) is presen...
Article
Full-text available
In the title molecular salt, C 15 H 22 N ⁺ ·I ⁻ , the fused-ring system is slightly puckered [dihedral angle between the five- and six-membered rings = 3.43 (8)°]. In the crystal, very weak C—H...I interactions link the cations to the anions. Photophysical data for the title salt in different solvents are presented.
Patent
Full-text available
INPI - Instituto Nacional da Propriedade Industrial Patent application: 06/10/2008 Grant of patent: 28/08/2018
Article
Silica hollow spheres are obtained as micro‐sized containers with magnetic‐field‐induced mobility. The completely empty hollow spheres are proved accessible with features of confined environment, where an unexpected structured fluorescence emission with large Stokes' shift is observed. This multifunctional system is achieved through a controllable...
Article
This work describes the synthesis of two sets of photoactive compounds with π-extended conjugation developed from a quinoxaline core condensed from an ortho-diamine and 1,2-diketone and followed by a Sonogashira coupling reaction. The electrochemical, photophysical and thermal properties of these compounds were evaluated. Thermogravimetric analysis...
Article
Investigations focused on the interactions of nanoparticles with lectins are relevant since it is well accepted that such proteins can be recognized by carbohydrates as parts of cell membranes. This can ultimately enhance the cellular uptake of the produced assemblies. In this framework, the physical interactions of phosphatidylcholine (PC) liposom...
Article
New hybrid materials using kaolin and the organosilicas methyl-polysiloxane (MK), methyl-phenyl-polysiloxane (H44), tetraethyl-ortho-silicate (TEOS) and 3-amino- propyl-triethoxysilane (APTES) were obtained by sol-gel process. These materials presented specific surfaces areas (S BET ) in the range of 20-530 m2 g -1 . Scanning electron microscopy (S...
Article
Full-text available
Correction for ‘Dipolar vinyl sulfur fluorescent dyes. Synthesis and photophysics of sulfide, sulfoxide and sulfone based D–π–A compounds’ by Matias Monçalves et al. , RSC Adv. , 2017, 7 , 8832–8842.
Article
Natural clay was grafted with 3-aminopropyl-trietoxisilane (APTES) for obtaining an organic-inorganic hybrid material. This material was successfully used as adsorbent for removal of Acid Red 1 (AR-1) and Acid Green 25 (AG-25) anionic dyes from aqueous solutions. This work demonstrates the effect of APTES concentration on the hydrophobic/hydrophili...
Article
A series of amino acid-derived 1,2,3-triazoles presenting the amino acid and the aromatic moieties connected by a triazole-4-carboxylate spacer is discussed in this work. These compounds were achieved in good yields by organocatalytic enamine−azide [3+2] cycloadditions. One of the molecules obtained, bearing a 7-chloroquinoline moiety was photoacti...
Article
This work presents the determination of the acidity strengths at the electronic ground and excited states (pKa and pKa*) of three flavonol derivatives using the electronic absorption and fluorescence emission spectroscopies. The differences of the pKa and pKa* values were sucessfully correlated to the molecular structures according to the substitut...