Editing Photochemical Reduction of Carbon Dioxide to Formic Acid using Ruthenium(II)-Based Catalysts and Visible Light

{{BaseTemplate}}
[[Category:Photocatalytic CO2 conversion to HCOOH]]
{{#doiinfobox: 10.1002/cctc.201500494 }}{{FaultyMolecule}}

=== Abstract ===

==== Summary ====
A photochemical reduction of CO<sub>2</sub> to formic acid was shown using a system containing an iridium-based photosensitizer, ruthenium photocatalyst and triethanolamine as the electron donor. Turnover numbers up to 526 and a selectivity of 80% towards formic acid were observed if the reaction was performed with [Ir(ppy)<sub>2</sub>(bpy)]PF<sub>6</sub> ({{#moleculelink:|link=RJJGJTKSOSSNNL-UHFFFAOYSA-N|image=false|width=300|height=200}}) as the photosensitizer and [Ru(bpy)<sub>2</sub>(Cl)(CO)]PF<sub>6</sub> ({{#moleculelink: |link=WUXWMOMXGWJDBM-UHFFFAOYSA-M|image=false|width=300|height=200}}) as the catalyst.  The experiments were conducted under irradiation with Hg-lamp equipped with a ''λ''=400–700 nm filter.

==== Advances and special progress ====
The employed photocatalytic system showed activity for the photoreduction of Na<sub>2</sub>CO<sub>3</sub> to formic acid as well. A TON of 53 was observed after 5h reaction time.

==== Additional remarks ====
Experiments using different electron and proton donors such as triethylamine (TEA) and 1-benzyl-1,4-dihydronicotinamide (BNAH) were unsuccessful as the observed activities were lower than those obtained in the presence of TEOA.

=== Content of the published article in detail ===
The article contains results for the reduction of CO2 to formic under visible-light catalysis using ruthenium complexes as catalysts, the iridium complex [Ir(ppy)<sub>2</sub>(bpy)]PF<sub>6</sub> ({{#moleculelink:|link=RJJGJTKSOSSNNL-UHFFFAOYSA-N|image=false|width=300|height=200}}) as a photosensitizer and triethanolamine as the electron donor. The catalytic system performs best (referring to the TON of HCOOH production) with [Ru(bpy)<sub>2</sub>(Cl)(CO)]PF<sub>6</sub> ({{#moleculelink: |link=WUXWMOMXGWJDBM-UHFFFAOYSA-M|image=false|width=300|height=200}}) as photocatalyst.

==== Catalysts ====
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  -INDIGO-01122412122D

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M  V30 6 C 7.417 -5.12879 0.0 0
M  V30 7 C 8.91079 -3.39942 0.0 0
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M  V30 20 C 10.4288 -7.69803 0.0 0
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M  V30 23 C 8.93404 -8.56983 0.0 0
M  V30 24 C 9.68611 -8.99663 0.0 0
M  V30 25 Ru 9.65664 -5.53338 0.0 0 CHG=2
M  V30 26 Cl 10.9874 -4.79065 0.0 0 CHG=-1
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M  V30 END ATOM
M  V30 BEGIN BOND
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M  V30 29 10 25 14
M  V30 30 10 25 4
M  V30 31 10 26 25
M  V30 32 10 27 25
M  V30 END BOND
M  V30 END CTAB
M  END
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  -INDIGO-07282310362D

  0  0  0  0  0  0  0  0  0  0  0 V3000
M  V30 BEGIN CTAB
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M  V30 BEGIN ATOM
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M  V30 23 C 6.8333 -9.30464 0.0 0
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M  V30 25 Ru 7.72682 -5.67729 0.0 0
M  V30 26 O 9.20801 -4.93397 0.0 0
M  V30 27 C 9.70801 -5.8 0.0 0
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M  V30 END ATOM
M  V30 BEGIN BOND
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M  V30 6 1 6 4
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M  V30 17 1 14 15
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M  V30 29 10 25 14
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M  V30 31 1 26 27
M  V30 32 1 27 28
M  V30 33 2 27 29
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M  V30 END BOND
M  V30 END CTAB
M  END
</chemform><chemform smiles="C1C=CN2[Ru+2]([C-]#[O+])([Cl-])3(N4C=CC=CC=4C4C=CC=CN=43)N3=CC=CC=C3C=2C=1.F[P-](F)(F)(F)(F)F" inchikey="QJMAHGUIKKRXBN-UHFFFAOYSA-M" inchi="1S/2C10H8N2.CO.ClH.F6P.Ru/c2*1-3-7-11-9(5-1)10-6-2-4-8-12-10;1-2;;1-7(2,3,4,5)6;/h2*1-8H;;1H;;/q;;;;-1;+2/p-1" float="none" width="200" height="200">
  -INDIGO-02262411182D

  0  0  0  0  0  0  0  0  0  0  0 V3000
M  V30 BEGIN CTAB
M  V30 COUNTS 35 39 0 0 0
M  V30 BEGIN ATOM
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M  V30 2 C 9.3939 -4.28472 0.0 0
M  V30 3 C 8.65956 -3.85983 0.0 0
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M  V30 23 C 10.1535 -8.94508 0.0 0
M  V30 24 C 10.8931 -9.36485 0.0 0
M  V30 25 Ru 10.8641 -5.90948 0.0 0 CHG=2
M  V30 26 Cl 12.2323 -4.95054 0.0 0 CHG=-1
M  V30 27 C 12.2815 -6.62253 0.0 0 CHG=-1
M  V30 28 O 13.1332 -7.1143 0.0 0 CHG=1
M  V30 29 F 13.8741 -4.45053 0.0 0
M  V30 30 P 14.7258 -3.95877 0.0 0 CHG=-1
M  V30 31 F 15.5776 -4.45053 0.0 0
M  V30 32 F 14.7258 -2.97524 0.0 0
M  V30 33 F 13.8741 -3.46701 0.0 0
M  V30 34 F 15.5776 -3.46701 0.0 0
M  V30 35 F 14.7258 -4.9423 0.0 0
M  V30 END ATOM
M  V30 BEGIN BOND
M  V30 1 2 3 1
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M  V30 3 1 1 5
M  V30 4 1 2 3
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M  V30 6 1 6 4
M  V30 7 1 2 7
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M  V30 18 2 17 18
M  V30 19 1 18 16
M  V30 20 1 16 19
M  V30 21 2 21 19
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M  V30 23 1 19 23
M  V30 24 1 20 21
M  V30 25 2 23 24
M  V30 26 1 24 22
M  V30 27 10 11 25
M  V30 28 10 25 21
M  V30 29 10 25 14
M  V30 30 10 25 4
M  V30 31 10 25 26
M  V30 32 10 25 27
M  V30 33 3 27 28
M  V30 34 1 29 30
M  V30 35 1 30 31
M  V30 36 1 30 32
M  V30 37 1 30 33
M  V30 38 1 30 34
M  V30 39 1 30 35
M  V30 END BOND
M  V30 END CTAB
M  END
</chemform><chemform smiles="C1C=CN2[Ru+2]([C-]#[O+])(O([H])[H])3(N4C=CC=CC=4C4C=CC=CN=43)N3=CC=CC=C3C=2C=1.F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F" inchi="1S/2C10H8N2.CO.2F6P.H2O.Ru/c2*1-3-7-11-9(5-1)10-6-2-4-8-12-10;1-2;2*1-7(2,3,4,5)6;;/h2*1-8H;;;;1H2;/q;;;2*-1;;+2" inchikey="CPFZZAZNEQBLAC-UHFFFAOYSA-N" height="200px" width="300px" float="none">
  -INDIGO-02152416342D

  0  0  0  0  0  0  0  0  0  0  0 V3000
M  V30 BEGIN CTAB
M  V30 COUNTS 44 47 0 0 0
M  V30 BEGIN ATOM
M  V30 1 C 5.62242 -3.98512 0.0 0
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M  V30 31 F 11.5741 -4.15053 0.0 0
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M  V30 END ATOM
M  V30 BEGIN BOND
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M  V30 6 1 6 4
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M  V30 9 2 10 8
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M  V30 42 1 38 39
M  V30 43 1 39 40
M  V30 44 1 39 41
M  V30 45 1 39 42
M  V30 46 1 39 43
M  V30 47 1 39 44
M  V30 END BOND
M  V30 END CTAB
M  END
</chemform><chemform smiles="" inchi="" inchikey="WYUQMBQARQRVFF-UHFFFAOYSA-N" height="200px" width="300px" float="none"></chemform><chemform smiles="C1C=CN2[Ru+2]([C-]#[O+])([H-])3(N4C=CC=CC=4C4C=CC=CN=43)N3=CC=CC=C3C=2C=1.F[P-](F)(F)(F)(F)F" inchi="1S/2C10H8N2.CO.F6P.Ru.H/c2*1-3-7-11-9(5-1)10-6-2-4-8-12-10;1-2;1-7(2,3,4,5)6;;/h2*1-8H;;;;/q;;;-1;+2;-1" inchikey="HJTHNVDYVJWKQG-UHFFFAOYSA-N" height="200px" width="300px" float="none">
  -INDIGO-02262411182D

  0  0  0  0  0  0  0  0  0  0  0 V3000
M  V30 BEGIN CTAB
M  V30 COUNTS 35 39 0 0 0
M  V30 BEGIN ATOM
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M  V30 19 C 6.80206 -7.71546 0.0 0
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M  V30 21 N 7.5385 -7.28895 0.0 0
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M  V30 23 C 6.80346 -8.57008 0.0 0
M  V30 24 C 7.54314 -8.98985 0.0 0
M  V30 25 Ru 7.51415 -5.53448 0.0 0 CHG=2
M  V30 26 H 8.88229 -4.57554 0.0 0 CHG=-1
M  V30 27 C 8.93149 -6.24753 0.0 0 CHG=-1
M  V30 28 O 9.78318 -6.7393 0.0 0 CHG=1
M  V30 29 F 10.5241 -4.07553 0.0 0
M  V30 30 P 11.3758 -3.58377 0.0 0 CHG=-1
M  V30 31 F 12.2276 -4.07553 0.0 0
M  V30 32 F 11.3758 -2.60024 0.0 0
M  V30 33 F 10.5241 -3.09201 0.0 0
M  V30 34 F 12.2276 -3.09201 0.0 0
M  V30 35 F 11.3758 -4.5673 0.0 0
M  V30 END ATOM
M  V30 BEGIN BOND
M  V30 1 2 3 1
M  V30 2 2 4 2
M  V30 3 1 1 5
M  V30 4 1 2 3
M  V30 5 2 5 6
M  V30 6 1 6 4
M  V30 7 1 2 7
M  V30 8 2 9 7
M  V30 9 2 10 8
M  V30 10 1 7 11
M  V30 11 1 8 9
M  V30 12 2 11 12
M  V30 13 1 12 10
M  V30 14 2 15 13
M  V30 15 2 16 14
M  V30 16 1 13 17
M  V30 17 1 14 15
M  V30 18 2 17 18
M  V30 19 1 18 16
M  V30 20 1 16 19
M  V30 21 2 21 19
M  V30 22 2 22 20
M  V30 23 1 19 23
M  V30 24 1 20 21
M  V30 25 2 23 24
M  V30 26 1 24 22
M  V30 27 10 11 25
M  V30 28 10 25 21
M  V30 29 10 25 14
M  V30 30 10 25 4
M  V30 31 10 25 26
M  V30 32 10 25 27
M  V30 33 3 27 28
M  V30 34 1 29 30
M  V30 35 1 30 31
M  V30 36 1 30 32
M  V30 37 1 30 33
M  V30 38 1 30 34
M  V30 39 1 30 35
M  V30 END BOND
M  V30 END CTAB
M  END
</chemform>

==== Photosensitizer ====
<chemform smiles="C1C=C[C-]2[Ir+3]3([C-]4C=CC=CC=4C4C=CC=CN=43)3(N4=CC=CC=C4C4C=CC=CN=43)N3=CC=CC=C3C=2C=1.[P-](F)(F)(F)(F)(F)F" inchi="1S/2C11H8N.C10H8N2.F6P.Ir/c2*1-2-6-10(7-3-1)11-8-4-5-9-12-11;1-3-7-11-9(5-1)10-6-2-4-8-12-10;1-7(2,3,4,5)6;/h2*1-6,8-9H;1-8H;;/q2*-1;;-1;+3" inchikey="RJJGJTKSOSSNNL-UHFFFAOYSA-N" height="200px" width="300px" float="none">
  -INDIGO-08012317142D

  0  0  0  0  0  0  0  0  0  0  0 V3000
M  V30 BEGIN CTAB
M  V30 COUNTS 44 51 0 0 0
M  V30 BEGIN ATOM
M  V30 1 C 4.03485 -3.90007 0.0 0
M  V30 2 C 5.76515 -3.89959 0.0 0
M  V30 3 C 4.90164 -3.39997 0.0 0
M  V30 4 C 5.76515 -4.90053 0.0 0 CHG=-1
M  V30 5 C 4.03485 -4.90502 0.0 0
M  V30 6 C 4.90382 -5.40003 0.0 0
M  V30 7 C 6.63141 -3.39999 0.0 0
M  V30 8 C 7.49583 -1.90109 0.0 0
M  V30 9 C 6.63149 -2.39928 0.0 0
M  V30 10 C 8.36278 -2.40138 0.0 0
M  V30 11 N 7.50182 -3.90229 0.0 0
M  V30 12 C 8.3649 -3.39706 0.0 0
M  V30 13 C 4.08485 -6.82507 0.0 0
M  V30 14 C 5.81515 -6.82459 0.0 0 CHG=-1
M  V30 15 C 4.95164 -6.32497 0.0 0
M  V30 16 C 5.81515 -7.82553 0.0 0
M  V30 17 C 4.08485 -7.83002 0.0 0
M  V30 18 C 4.95382 -8.32503 0.0 0
M  V30 19 C 6.68166 -8.3247 0.0 0
M  V30 20 C 8.41196 -8.32139 0.0 0
M  V30 21 N 7.54763 -7.82318 0.0 0
M  V30 22 C 8.41359 -9.32233 0.0 0
M  V30 23 C 6.6833 -9.32964 0.0 0
M  V30 24 C 7.55308 -9.82324 0.0 0
M  V30 25 C 9.35985 -3.77507 0.0 0
M  V30 26 C 11.0902 -3.77459 0.0 0
M  V30 27 C 10.2266 -3.27497 0.0 0
M  V30 28 C 11.0902 -4.77553 0.0 0
M  V30 29 N 9.35985 -4.78002 0.0 0
M  V30 30 C 10.2288 -5.27503 0.0 0
M  V30 31 C 10.2327 -6.27503 0.0 0
M  V30 32 C 11.105 -7.76933 0.0 0
M  V30 33 C 11.1014 -6.7717 0.0 0
M  V30 34 C 10.2405 -8.27372 0.0 0
M  V30 35 N 9.36465 -6.78143 0.0 0
M  V30 36 C 9.37498 -7.78146 0.0 0
M  V30 37 Ir 7.55 -5.775 0.0 0 CHG=3
M  V30 38 P 13.517 -3.7 0.0 0 CHG=-1
M  V30 39 F 14.383 -3.2 0.0 0
M  V30 40 F 12.651 -3.2 0.0 0
M  V30 41 F 13.517 -4.7 0.0 0
M  V30 42 F 14.383 -4.2 0.0 0
M  V30 43 F 13.517 -2.7 0.0 0
M  V30 44 F 12.651 -4.2 0.0 0
M  V30 END ATOM
M  V30 BEGIN BOND
M  V30 1 2 3 1
M  V30 2 2 4 2
M  V30 3 1 1 5
M  V30 4 1 2 3
M  V30 5 2 5 6
M  V30 6 1 6 4
M  V30 7 1 2 7
M  V30 8 2 9 7
M  V30 9 2 10 8
M  V30 10 1 7 11
M  V30 11 1 8 9
M  V30 12 2 11 12
M  V30 13 1 12 10
M  V30 14 2 15 13
M  V30 15 2 16 14
M  V30 16 1 13 17
M  V30 17 1 14 15
M  V30 18 2 17 18
M  V30 19 1 18 16
M  V30 20 1 16 19
M  V30 21 2 21 19
M  V30 22 2 22 20
M  V30 23 1 19 23
M  V30 24 1 20 21
M  V30 25 2 23 24
M  V30 26 1 24 22
M  V30 27 2 27 25
M  V30 28 2 28 26
M  V30 29 1 25 29
M  V30 30 1 26 27
M  V30 31 2 29 30
M  V30 32 1 30 28
M  V30 33 1 30 31
M  V30 34 2 33 31
M  V30 35 2 34 32
M  V30 36 1 31 35
M  V30 37 1 32 33
M  V30 38 2 35 36
M  V30 39 1 36 34
M  V30 40 10 11 37
M  V30 41 10 37 29
M  V30 42 10 35 37
M  V30 43 10 37 21
M  V30 44 10 14 37
M  V30 45 10 37 4
M  V30 46 1 38 39
M  V30 47 1 38 40
M  V30 48 1 38 41
M  V30 49 1 38 42
M  V30 50 1 38 43
M  V30 51 1 38 44
M  V30 END BOND
M  V30 END CTAB
M  END
</chemform>

==== Investigations ====
{{#experimentlist:|form=Photocatalytic_CO2_conversion_experiments|name=Table 1}}

{{#experimentlist:|form=Photocatalytic_CO2_conversion_experiments|name=Table 2}}

{{#experimentlist:|form=Cyclic_Voltammetry_experiments|name=Table 3 - CV}}

==== Sacrificial electron donor ====
In this study, the experiments were done with the sacrificial electron donor TEOA ([[Molecule:100507|100507]]).

==== Additives ====
No additives were used in the described experiments.