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
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.
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.
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.
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.
