Photosensitized activation of diazonium derivatives for C–B bond formation

Ripak, Alexia; Kreijger, Simon De; Sampaio, Renato N.; Vincent, Cooper A.; Cauët, Émilie; Jabin, Ivan; Tambar, Uttam K.; Elias, Benjamin; Troian‐Gautier, Ludovic

doi:10.1016/j.checat.2022.100490

Cited by 22 publications

(39 citation statements)

References 84 publications

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“…Finally, cage-escape yields, i.e., the efficiency with which the geminate radical pair (i.e., the monoreduced binuclear iridium photosensitizer and oxidized halide) separates after excited-state electron transfer, was quantified using nsTAS . Quantifying this process is of interest because it was shown to impact the subsequent reactions that can be performed using these solvent-separated radicals. − Here, cage-escape yields were determined by comparative actinometry using eqs and with [Ru(bpy) 3 ] 2+ as the actinometer Φ CE = Φ % PL quenched Φ = true( normalΔ A PS − normalΔ ε PS − normalΔ A ES ref normalΔ ε ES ref true) true( 1 − 10 − Abs ref ( λ exc ) 1 − 10 − Abs PS ( λ exc ) true) …”

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confidence: 99%

Chloride, Bromide, and Iodide Photooxidation in Acetonitrile/Water Mixtures Using Binuclear Iridium(III) Photosensitizers

De Kreijger,

Elias,

Troian-Gautier

2023

Inorg. Chem.

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Two iridium(III) binuclear photosensitizers, [Ir-(dFCF 3 ppy) 2 (N−N)Ir(dFCF 3 ppy) 2 ] 2+ , where N−N is tetrapyrido[3,2-a:2′,3′-c:3″,2″-h:2‴,3‴-j]phenazine (Ir-TPPHZ) and 1,4,5,8-tetraazaphenanthrene[9,10-b]-1,4,5,8,9,12-hexaazatriphenylene (Ir-TAPHAT) are reported for iodide, bromide, and chloride photooxidation in acetonitrile and acetonitrile/water mixtures using blue-light irradiation. Excited-state reduction potentials E red * of +2.02 and +2.09 V vs NHE were determined for Ir-TPPHZ and Ir-TAPHAT, respectively. Both photosensitizers' excited states were efficiently quenched by iodide, bromide, and chloride with quenching rate constants in the (3.5−9.2) × 10 10 and (0.0036−2.9) × 10 10 M −1 s −1 ranges in neat acetonitrile and acetonitrile/water mixtures, respectively. Nanosecond transient absorption spectroscopy provided unambiguous evidence of reductive excited-state electron transfer, with all halides in the solvent mixtures containing up to 50% water. Cage-escape yields were large (55−96%) in acetonitrile and dropped below 32% in 50:50 acetonitrile/water mixtures.

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confidence: 99%

Chloride, Bromide, and Iodide Photooxidation in Acetonitrile/Water Mixtures Using Binuclear Iridium(III) Photosensitizers

De Kreijger,

Elias,

Troian-Gautier

2023

Inorg. Chem.

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“…As hinted above, the photografting of diazonium salts and particularly of 4‐nitrobenzenediazonium (4‐NBD) has been widely reported in literature [1,29,30] . recently the detailed analysis of the photosensitized activation of diazonium salts has been released [31] . For the sake of comparison, we reported the results obtained with 4‐nitrobenzene diazonium tetrafluoroborate under the same conditions used for arylazo sulfonates.…”

Section: Resultsmentioning

confidence: 94%

“…[1,29,30] recently the detailed analysis of the photosensitized activation of diazonium salts has been released. [31] For the sake of comparison, we reported the results obtained with 4-nitrobenzene diazonium tetrafluoroborate under the same conditions used for arylazo sulfonates. The IRRAS spectrum corresponds to grafted nitrophenyl moieties with the characteristic nitro vibrations at 1527 and 1350 cm À 1 .…”

Section: Photografting Of 4-nitrobenzenediazonium Saltmentioning

confidence: 99%

Selective N_sp2‐ and C_sp2‐ Photografting of Au‐Surface by Aryldiazonium Salts and Arylazo Sulfonates

Nicchio

Médard

Decorse

et al. 2023

Chemistry A European J

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Arylazo sulfonates (ArÀ N=NÀ SO 3 Na) have been found to undergo photografting on gold surface through both AuÀ N sp2 À and AuÀ C sp2 À bond formation. The functionalized materials have been fully characterized by infrared reflection absorption spectroscopy (IRRAS), Raman, XPS, DFT calculations and UV-Vis absorption spectroscopy. These methods permit to evidence aromatic substituents (IRRAS), the AuÀ N=N signature (Raman and XPS spectroscopy), and the bond dissociation energy values of the two linkages (DFT calculation). The grafting proceeds through two competitive paths, namely a stepwise reaction involving an aryl radical (for the formation of the AuÀ Ar bonds) and a concerted reaction on the surface of gold (for AuÀ N=NÀ Ar bond formation). The occurrence of an aryl radical upon irradiation has been fully evidenced by EPR spectroscopy. Finally, E/Z photoisomerisation of the N=N bonds present on prepared few layer films has been observed by means of UV-Vis absorption spectroscopy.

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“…Although comparatively poor yields and conversions were obtained for both the Fe-PCs, this report showcases yet another example of the application of iron compounds for photoredox catalysis. 93 Photocatalysis Driven by the Relatively Short-Lived CT States of [Fe(btz) 3 ](PF 6 ) 3 . Due to the relatively short 2 LMCT lifetime (τ = 100 ps) of the mesoionic carbene complex [Fe(III)(btz) 3 ](PF 6 ) 3 (11, Figure 4), 82 the bimolecular quenching had not been studied.…”

Section: ■ Application Of the Charge-transfer State Of Iron Complexes...mentioning

confidence: 99%

“…In a very recent publication by the group of Troian-Gautier, complex 12 and its dibromo-substituted analogue ([Fe(Br-phtmeimb) 2 ] + ), along with other TM complexes, were investigated as PCs for the borylation of aryldiazonium salts under irradiation (525 nm). Although comparatively poor yields and conversions were obtained for both the Fe-PCs, this report showcases yet another example of the application of iron compounds for photoredox catalysis …”

Section: Application Of the Charge-transfer State Of Iron Complexes I...mentioning

confidence: 99%

Iron Photoredox Catalysis–Past, Present, and Future

et al. 2023

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Photoredox catalysis of organic reactions driven by iron has attracted substantial attention throughout recent years, due to potential environmental and economic benefits. In this Perspective, three major strategies were identified that have been employed to date to achieve reactivities comparable to the successful noble metal photoredox catalysis: (1) Direct replacement of a noble metal center by iron in archetypal polypyridyl complexes, resulting in a metal-centered photofunctional state. (2) In situ generation of photoactive complexes by substrate coordination where the reactions are driven via intramolecular electron transfer involving charge-transfer states, for example, through visible-light-induced homolysis. (3) Improving the excited-state lifetimes and redox potentials of the charge-transfer states of iron complexes through new ligand design. We seek to give an overview and evaluation of recent developments in this rapidly growing field and, at the same time, provide an outlook on the future of iron-based photoredox catalysis.

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Photosensitized activation of diazonium derivatives for C–B bond formation

Cited by 22 publications

References 84 publications

Chloride, Bromide, and Iodide Photooxidation in Acetonitrile/Water Mixtures Using Binuclear Iridium(III) Photosensitizers

Chloride, Bromide, and Iodide Photooxidation in Acetonitrile/Water Mixtures Using Binuclear Iridium(III) Photosensitizers

Selective N_sp2‐ and C_sp2‐ Photografting of Au‐Surface by Aryldiazonium Salts and Arylazo Sulfonates

Iron Photoredox Catalysis–Past, Present, and Future

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Photosensitized activation of diazonium derivatives for C–B bond formation

Cited by 22 publications

References 84 publications

Chloride, Bromide, and Iodide Photooxidation in Acetonitrile/Water Mixtures Using Binuclear Iridium(III) Photosensitizers

Chloride, Bromide, and Iodide Photooxidation in Acetonitrile/Water Mixtures Using Binuclear Iridium(III) Photosensitizers

Selective Nsp2‐ and Csp2‐ Photografting of Au‐Surface by Aryldiazonium Salts and Arylazo Sulfonates

Iron Photoredox Catalysis–Past, Present, and Future

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Selective N_sp2‐ and C_sp2‐ Photografting of Au‐Surface by Aryldiazonium Salts and Arylazo Sulfonates