147804-55-5Relevant articles and documents
Spectroscopic and photophysical properties of mono- and dithiosubstituted BODIPY dyes
Zlati?, Katarina,Ayouchia, Hicham Ben El,Anane, Hafid,Mihaljevi?, Branka,Basari?, Nikola,Rohand, Taoufik
, (2020)
A series of BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) dyes, substituted at the 3 and 5 positions was synthesized and their spectral and photophysical properties were investigated in solvents of different polarity and polarizability. All compound
A BODIPY analogue from the tautomerization of sodium 3-oxide BODIPY
Chen, Peng-Zhong,Zheng, Hai-Rong,Niu, Li-Ya,Chen, Yu-Zhe,Wu, Li-Zhu,Tung, Chen-Ho,Yang, Qing-Zheng
, p. 631 - 635 (2015)
Abstract The introduction of hydroxy group to the 3- or 5-position of 4,4-difluoro-4-bora-3a,4a-diazaindacene (BODIPY) results in unexpected tautomerization to BDPONa with interesting structural and photophysical properties. The core of BDPONa is an anion
One-pot synthesis of bisindolylmethanes from benzyl alcohols and indoles using catalytic iodine and molecular oxygen under visible light irradiation
Nobuta, Tomoya,Fujiya, Akitoshi,Tada, Norihiro,Miura, Tsuyoshi,Itoh, Akichika
, p. 2975 - 2979 (2012)
Bisindolylmethanes can be directly synthesized from benzyl alcohol and indole in up to 86% yield using molecular oxygen, visible light, and catalytic iodine, which serves as both an oxidant and a Lewis acid. Georg Thieme Verlag KG · Stuttgart · New York.
Synthesis of porphyrin dyads with potential use in solar energy conversion
Fungo, Fernando,Otero, Luis A.,Sereno, Leonides,Silber, Juana J.,Durantini, Edgardo N.
, p. 645 - 650 (2000)
A convenient procedure for the synthesis of porphyrin derivative dyads is described. The dyads consist of a free base porphyrin covalently linked to a zinc porphyrin or ferrocene by an amide bond. 5-(4-Substituted phenyl)- 10,15,20-tris(4-methylphenyl) po
Excitation-Wavelength-Dependent Light-Induced Electron Transfer and Twisted Intramolecular Charge Transfer in N, N-Bis(4′- tert-butylbiphenyl-4-yl)aniline Functionalized Borondipyrromethenes
Gangada, Suneel,Ramnagar, Ramya Athira,Sangolkar, Akanksha Ashok,Pawar, Ravinder,Nanubolu, Jagadeesh Babu,Roy, Partha,Giribabu, Lingamallu,Chitta, Raghu
, p. 9738 - 9750 (2020)
A series of bis(4′-tert-butylbiphenyl-4-yl)aniline (BBA) functionalized borondipyrromethene (BODIPY) dyads, Dyads 1-3, containing the BBA group tethered to BODIPY moiety either directly or through a phenyl or alkynyl phenyl spacers are synthesized, and the light-mediated charge transfer within the chromophores has been systematically investigated. The crystal structure of Dyad-1 showed a tilt of 44.2° between the BODIPY and BBA molecular planes and intermolecular C-H···πinteractions with these moieties. Cyclic voltammetric and computational studies showed that the BBA moiety can act as the electron donor (D) and BODIPY as the electron acceptor (A) and the optical absorption studies revealed that an increase in the conjugation of the linker from Dyad-1 to Dyad-2 resulted in bathochromic shifts. Steady-state fluorescence studies involving photoexcitation of the BBA moiety at 326 nm resulted in the decrease in fluorescence intensity of the BBA, indicating the possibility of sequential occurrence of faster photoinduced energy transfer (PEnT) followed by the photoinduced electron transfer (PET) or solely PET within the dyads, and the driving forces of the charge separation were calculated to be exothermic in all of the employed solvents. Parallel time-resolved fluorescence experiments involving the excitation of BBA moiety also supported the occurrence of charge separation in these dyads. Interestingly, excitation of the BODIPY moiety of Dyad-1 and Dyad-2 at 490 nm in solvents of increasing polarity leads to a red-shifted BODIPY emission with weakened intensity. This spectral behavior indicated the occurrence of emission from the locally excited (LE) state in nonpolar solvents, whereas formation of an LE state followed by the rotation of the chromophores at the D-A bond leads to a low energy twisted intramolecular charge transfer state (TICT), resulting in a charge-separated state BBA+?-BODIPY-? in polar solvents. Furthermore, the hydrophobicity studies involving the solutions of dyads in admixtures of polar tetrahydrofuran (THF) and nonpolar hexanes revealed that when the fraction of hexanes in these mixtures is increased, the emission of BODIPY moiety was observed to be blue-shifted and exhibited enhanced intensity supporting the occurrence of TICT in these dyads.
A new chiral boron-dipyrromethene (BODIPY)-based fluorescent probe: molecular docking, DFT, antibacterial and antioxidant approaches
Alnoman, Rua B.,Parveen, Shazia,Hagar, Mohamad,Ahmed, Hoda A.,Knight, Julian G.
, p. 5429 - 5442 (2020)
A new chiral BODIPY-based fluorescent compound, 5-bromo-4,4-difluoro-3(S)-1-phenylethyl)amino) BODIPY, 4 was synthesized for biomedical applications. Optical, antimicrobial, antioxidant properties of the compound 4 are investigated. The partition coefficient suggested that the compound 4 has the potential to be developed as an active antibacterial and antioxidant candidate. In this context, antibacterial assay was carried out for compound 4 against various bacterial strains, revealing maximum inhibition zone (24 ± 2.19 mm) in Escherichia coli. Moreover, results of antioxidant activity of compound 4 revealed IC50 values to be greater than ascorbic acid. Molecular docking has given brief insight about the binding of the compound 4, suggesting that it has a strong potential to inhibit bacterial target enzymes viz., DNA gyrase, enzymes in the type II fatty acid synthesis and Ddl (d-alanine: d-alanine ligase) in peptidoglycan synthesis. The molecular geometry and electrostatic potential of compound 4, was established by DFT (Density Functional Theory) calculations. AbbreviationsBBB blood?brain barrierBDE bond dissociation energyBODIPY boron–dipyrromethaneDdl D-alanine:D-alanine ligaseDDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinoneDFT density functional theoryDNA deoxyribonucleic acidDPPH 1,1?diphenyl?2?picrylhydrazylNBSN-bromo succinimideROS reactive oxygen speciesUV–vis ultraviolet–visibleFMO frontier molecular orbitalsHOMO highest occupied molecular orbitalLUMO lowest unoccupied molecular orbital Communicated by Ramaswamy H. Sarma.
An unexpected coupling-reduction tandem reaction for the synthesis of alkenyl-substituted BODIPYs
Teng, Kun-Xu,Niu, Li-Ya,Li, Jie,Jia, Lu,Yang, Qing-Zheng
, p. 13761 - 13764 (2019)
We report an unexpected coupling-reduction tandem reaction as a general and efficient one-pot synthesis of alkenyl-substituted boron dipyrromethene (BODIPY) from chlorinated-BODIPY and alkyne. This unique synthesis combined the Sonogashira coupling reaction and reduction reaction without adding an additional reagent, which shows higher yields, broader substrate scope and faster reaction rate compared with the conventional methods of the Knoevenagel reaction and Heck coupling reaction.
Porphyrin–schiff base conjugates bearing basic amino groups as antimicrobial phototherapeutic agents
Alvarez, María G.,Durantini, Edgardo N.,Durantini, Javier E.,Milanesio, María E.,Pérez, María E.,Reynoso, Eugenia
supporting information, (2021/10/05)
New porphyrin–Schiff base conjugates bearing one (6) and two (7) basic amino groups were synthesized by condensation between tetrapyrrolic macrocycle-containing amine functions and 4-(3-(N,N-dimethylamino)propoxy)benzaldehyde. This approach allowed us to easily obtain porphyrins substituted by positive charge precursor groups in aqueous media. These compounds showed the typical Soret and four Q absorption bands with red fluorescence emission (ΦF ~ 0.12) in N,N-dimethylformamide. Porphyrins 6 and 7 photosensitized the generation of O2 (1?g) (Φ? ~ 0.44) and the photo-oxidation of L-tryptophan. The decomposition of this amino acid was mainly mediated by a type II photoprocess. Moreover, the addition of KI strongly quenched the photodynamic action through a reaction with O2 (1?g) to produce iodine. The photodynamic inactivation capacity induced by porphyrins 6 and 7 was evaluated in Staphylococcus aureus, Escherichia coli, and Candida albicans. Furthermore, the photoinactivation of these microorganisms was improved using potentiation with iodide anions. These porphyrins containing basic aliphatic amino groups can be protonated in biological systems, which provides an amphiphilic character to the tetrapyrrolic macrocycle. This effect allows one to increase the interaction with the cell wall, thus improving photocytotoxic activity against microorganisms.
Oxidative c-h/c-h coupling of dipyrromethanes with azines by tio2-based photocatalytic system. Synthesis of new bodipy dyes and their photophysical and electrochemical properties
Chupakhin, Oleg N.,Dorosheva, Irina B.,Gadomska, Anna V.,Kim, Gregory A.,Nikolenko, Lyubov M.,Pevtsov, Dmitry N.,Razumov, Vladimir F.,Rempel, Andrey A.,Semenov, Maksim V.,Shchepochkin, Alexander V.,Tovstun, Sergey A.,Trestsova, Maria A.,Utepova, Irina A.
, (2021/09/18)
Oxidative C-H/C-H coupling reactions of dipyrromethanes with azines in the presence of a heterophase oxidative photocatalytic system (O2/TiO2/visible light irradiation) were carried out. As a result of cyclization of obtained compounds with boron trifluoride etherate, new hetaryl-containing derivatives of 4,4-difluoro-4-boron-3a,4a-diaza-s-indacene were synthesized. For the obtained compounds, absorption and luminescence spectra, quantum yields of luminescence as well as cyclic volt-amperograms were measured.
K2S2O8mediated synthesis of 5-Aryldipyrromethanes and meso-substituted A4-Tetraarylporphyrins
Laha, Joydev K.,Hunjan, Mandeep Kaur
, p. 664 - 673 (2021/06/03)
The synthesis of dipyrromethanes from pyrrole and arylglyoxylic acids in the presence of K2S2O8at 90 C is reported affording dipyrromethanes in very good yields. Unlike an excess pyrrole traditionally used in dipyrromethane synthesis, the current method uses a stoichiometric amount of pyrrole avoiding any use of Br?nsted or Lewis acid. A gram scale synthesis of 5-phenyldipyrromethane is also achieved demonstrating potential scale up of dipyrromethanes using this method feasible. Subsequently, dipyrromethanes were converted to A4tetraarylporphyrins also in the presence of K2S2O8at 90C. A direct synthesis of A4-tetraphenylporphyrin from excess pyrrole and phenylglyoxylic acid in the presence of K2S2O8 at 90C is also reported.
