Nonlinear optical properties of multipyrrole dyes

Frenette, Mathieu; Hatamimoslehabadi, Maryam; Bellinger-Buckley, Stephanie; Laoui, Samir; Bag, Seema; Dantiste, Olivier; Rochford, Jonathan; Yelleswarapu, Chandra S.

doi:10.1016/j.cplett.2014.06.002

Cited by 49 publications

(21 citation statements)

References 38 publications

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“…[52] Furthermore, aza-BODIPYs have been proposed as photoactive components in photovoltaic devices [54][55][56] and nonlinear optical materials. [57] Our interesti ne fficient yet stable and modifiable organic triplet photosensitizes has lead us to the discoveryo fn ovel aza-BODIPYs. Herein, we report the synthesis and ac omprehensives tudy on the photophysical properties of as eries of iodinated aza-BODIPYs.…”

Section: Introductionmentioning

confidence: 99%

Visible‐Light Photoactive, Highly Efficient Triplet Sensitizers Based on Iodinated Aza‐BODIPYs: Synthesis, Photophysics and Redox Properties

Gut

Łapok

Drelinkiewicz

et al. 2017

Chemistry An Asian Journal

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As eries of novel iodinated NO 2 -substituted azaBODIPYs have been synthesized and characterized.H ighly desirable photophysical and photochemical properties were induced in NO 2 -substituted aza-BODIPYs by iodinationo ft he pyrrole rings. In particular, highv alues of singlet oxygen quantum yields (F D )r anging from 0.79 to 0.85 were measured. The photooxygenation process proceeds via aT ype II mechanism under the experimental conditions applied. The compounds studied exhibited an absorption band within the so-called "therapeutic window", with l max located between 645 nm to 672 nm. They were non-fluorescent at room temperature with excited singlet-state lifetimes within the picosecond range as measured by femtosecond transient absorption. Nanosecond laser flash photolysis experiments revealed T 1 !T n absorption spanning from ca. 400 nm to ca. 500 nm and allowedd etermination of the triplet-state lifetimes. The estimated triplet lifetimes (t T )i nd eaerated acetonitrile ranged between 2.74 msa nd 3.50 ms. As estimated by CV/DPV measurements, all iodinateda za-BODIPYs studied exhibited one irreversible oxidation and two quasireversible reductions processes. Estimation of the E HOMO gave the value of À6.06 to À6.26 eV while the E LUMO was found to be located at ca. À4.6 eV.T hermogravimetric (TGA) analysis revealed that iodinated aza-BODIPYs weres table up to approximately 300 8C. All compounds studied exhibit high photostability in toluene solution.

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Section: Introductionmentioning

confidence: 99%

Visible‐Light Photoactive, Highly Efficient Triplet Sensitizers Based on Iodinated Aza‐BODIPYs: Synthesis, Photophysics and Redox Properties

Gut

Łapok

Drelinkiewicz

et al. 2017

Chemistry An Asian Journal

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“…Owing to their advantageous photophysical properties (triplet lifetimes τ T , triplet state quantum yields Φ T and triplet state energies E T ) combined with tunable singlet oxygen quantum yields (Φ Δ ) and ability to absorb light from the “therapeutic window”, aza‐BODIPYs have been proposed as potential triplet photosensitizers for both anti ‐microbial and anti ‐cancer photodynamic therapy . Furthermore, aza‐BODIPYs were considered as fluorescent chemosensors for the detection of ammonia, cysteine, homocysteine and glutathione in living cells, Hg 2+ , F − , in vivo detection of H 2 S and NO, carbon dioxide, glucose in whole blood and pH‐sensitive sensors . Aza‐BODIPYs have also been tested as photoactive components in photovoltaic devices and nonlinear optical materials …”

Section: Introductionmentioning

confidence: 99%

Near‐Infrared Photoactive Aza‐BODIPY: Thermally Robust and Photostable Photosensitizer and Efficient Electron Donor

et al. 2020

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We report herein the synthesis of aza-BODIPY substituted with strongly electron-donating p-(diphenylamino)phenyl substituents (p-Ph 2 NÀ ) at 3,5-positions. The presence of p-Ph 2 NÀ groups lowers the energy of the singlet excited state (E s ) to 1.48 eV and induces NIR absorption with λ abs at 789 nm in THF. The compound studied is weakly emissive with the emission band (λ f ) at 837 nm and with the singlet lifetime (τ S ) equal to 100 ps. Nanosecond laser photolysis experiments of the aza-BODIPY in question revealed T 1 !T n absorption spanning from ca. 350-550 nm with the triplet lifetime (τ T ) equal to 21 μs. By introducing a heavy atom (Br) into the structure of the aza-BODIPY, we managed to turn it into a NIR operating photosensitizer. The photosensitized oxygenation of the model compound-diphenylisobenzofuran (DPBF)-proceedes via Type I and/or Type III mechanism without formation of singlet oxygen ( 1 O 2 ). As estimated by CV/DPV measurements, the p-Ph 2 NÀ substituted aza-BODIPYs studied exhibits oxidation processes at relatively low oxidation potentials (E ox 1 ), pointing to the very good electron-donating properties of these molecules. Extremely high photostability and thermal robustness up to approximately 300°C are observed for the p-Ph 2 NÀ substituted aza-BODIPYs. [a] Dr. . Synthesis of mono-bromo aza-BODIPY 7. Reaction conditions: a) acetyl chloride, ZnCl 2 , DCM, 0°C to reflux, 24 h, 45 %; b) 4-tert-butylbenzaldehyde, NaOH, EtOH, 0°C to RT, 24 h, 69 %; c) MeNO 2 , K 2 CO 3 , MeOH, reflux, 17 h, 79 % ; d) CH 3 COONH 4 ,n-butanol, 117°C, 3 h, 63 %; e) BF 3 · Et 2 O, DIPA, DCM, 1 h, 91 %; f) NBS, DCM, 2 h, 0°C, 96 %.ChemPhysChem Articles

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“…Aza‐BODIPY were tested as chemosensors for the detection of ammonia, cysteine, homocysteine and glutathione in living cells, Hg 2+ , F − , in vivo detection of H 2 S, [33] carbon dioxide, glucose in whole blood, detection of saxitoxin and pH‐sensitive sensors . Other applications of aza‐BODIPY encompass their utilization as photoactive components in photovoltaic devices and nonlinear optical materials …”

Section: Introductionmentioning

confidence: 99%

A Beneficial Effect of Bromination on the Photophysical and Photochemical Properties of Aza‐BODIPY Dyes with Electron‐Donating Groups

et al. 2019

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A series of aza-BODIPY dyes substituted with meta-(dimethylamino)phenyl groups were synthesized and their spectroscopic, photophysical, and electrochemical properties were compared. Highly desirable photophysical and photochemical properties were induced in meta-(Me 2 N)Ph-substituted aza-BODIPY by bromination of the aromatic rings at the 3 and 5 positions. In particular, high values of singlet oxygen quantum yields (Φ Δ ) were measured, ranging from 0.36 to 0.58. The photosensitized oxygenation process of a model compound -diphenylisobenzofuran (DPBF) -proceeds via a Type II mechanism for the di-bromo derivative, while for the tetra-bromo derivative a mixed mechanism involving both 1 O 2 and other reactive forms of oxygen formation (Type I and/or Type III) was detected. Nanosecond laser photolysis experiments of the brominated aza-BODIPYs revealed T 1 !T n absorption spanning from ca. 350 nm to ca. 510 nm with the triplet lifetimes (τ T ) ranged between 15.6 μs and 26.0 μs. The brominated aza-BODIPYs studied exhibited an absorption band within the so-called "therapeutic window", with λ abs located between 620 nm and 636 nm. As estimated by CV/ DPV measurements, the meta-(Me 2 N)Ph-substituted aza-BOD-IPYs studied exhibited a multi-electron oxidation processes at a relatively low oxidation potentials (E ox ), pointing to the very good electron-donating properties of these molecules. All compounds studied exhibited extremely high photostability and thermal stability.[a] M. Obłoza, Dr. Ł. Łapok, Prof. Dr. M. Nowakowska

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Nonlinear optical properties of multipyrrole dyes

Cited by 49 publications

References 38 publications

Visible‐Light Photoactive, Highly Efficient Triplet Sensitizers Based on Iodinated Aza‐BODIPYs: Synthesis, Photophysics and Redox Properties

Visible‐Light Photoactive, Highly Efficient Triplet Sensitizers Based on Iodinated Aza‐BODIPYs: Synthesis, Photophysics and Redox Properties

Near‐Infrared Photoactive Aza‐BODIPY: Thermally Robust and Photostable Photosensitizer and Efficient Electron Donor

A Beneficial Effect of Bromination on the Photophysical and Photochemical Properties of Aza‐BODIPY Dyes with Electron‐Donating Groups

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