Visible-Light-Driven Conversion of CO2 to CH4 with an Organic Sensitizer and an Iron Porphyrin Catalyst: Difference between revisions

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DOI 10.1021/jacs.8b09740
Authors Heng Rao, Chern-Hooi Lim, Julien Bonin, Garret M. Miyake, Marc Robert,
Submitted 07.12.2018
Published online 07.12.2018
Licenses -
Subjects Colloid and Surface Chemistry, Biochemistry, General Chemistry, Catalysis
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{{#doiinfobox: 10.1021/jacs.8b09740}}
{{DOI|doi=10.1021/jacs.8b09740}}


===Catalysts===
=== Abstract ===
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  -INDIGO-12132211272D


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==== Summary ====
M  V30 BEGIN CTAB
A photochemical reduction of CO<sub>2</sub> to CO and CH<sub>4</sub> was shown using the iron porphyrin catalyst {{#moleculelink:|link=LKNRTBVZMCBYCY-NGWNFTKISA-I|image=false|width=300|height=200}} in combination with the phenoxazine photosensitizers {{#moleculelink:|link=HPIOBCHPZVAATK-UHFFFAOYSA-N|image=false|width=300|height=200}} and {{#moleculelink:|link=IGGSSEOAGCUGDJ-UHFFFAOYSA-N|image=false|width=300|height=200}}. Turnover numbers (TONs) up to 149 for CO and 29 for CH<sub>4</sub> were reached. The experiments were conducted under visible-light irradiation (λ > 435 nm) with a tertiary amine (see section SEDs below) as sacrificial electron donor.  
M  V30 COUNTS 65 76 0 0 0
 
M  V30 BEGIN ATOM
==== Advances and special progress ====
M  V30 1 C 6.04424 -2.5609 0.0 0
This article contains the first demonstration for the reduction of CO<sub>2</sub> to CH<sub>4</sub> (complete 8e''<sup>–</sup>''/8H<sup>+</sup> reduction) by a combination of an earth-abundant metal catalyst and an organic dye. So far, similar systems were shown to induce 2e<sup>–</sup>/2H<sup>+</sup> reduction of CO<sub>2</sub> to CO or formic acid.  
M  V30 2 C 7.33133 -1.66667 0.0 0
 
M  V30 3 C 6.36602 -1.6242 0.0 0
==== Additional remarks ====
M  V30 4 C 7.56769 -2.60624 0.0 0
Methane was produced continuously (even after irradiation up to 4 days). The 8e''<sup>–</sup>''/8H<sup>+</sup> reduction efficiency strongly depends on the redox properties of the organic photosensitizer and acidity of the proton source. In additional experiments, CO was used as the gas resource. The system consisting of iron porphyrin catalyst {{#moleculelink:|link=LKNRTBVZMCBYCY-NGWNFTKISA-I|image=false|width=300|height=200}} in combination with the phenoxazine photosensitizer {{#moleculelink:|link=IGGSSEOAGCUGDJ-UHFFFAOYSA-N|image=false|width=300|height=200}} was able to produce CH<sub>4</sub> with a TON of 80 (85% selectivity, quantum yield: 0.47%).  
M  V30 5 N 6.78397 -3.14046 0.0 0
 
M  V30 6 C 4.63287 -3.92379 0.0 0
=== Content of the published article in detail ===
M  V30 7 C 4.532 -5.51407 0.0 0
The article contains results for the reduction of CO<sub>2</sub> and CO as feedstock gases. The catalytic system performs best (referring to the TON of CH<sub>4</sub> production) for CO as a feedstock.  
M  V30 8 N 5.16816 -4.74793 0.0 0
 
M  V30 9 C 3.63825 -5.15661 0.0 0
==== Catalysts ====
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M  V30 11 C 8.75201 -4.00987 0.0 0
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M  V30 16 C 7.01046 -7.93253 0.0 0
M  V30 17 C 5.78378 -6.99601 0.0 0
M  V30 18 C 6.03403 -7.92348 0.0 0
M  V30 19 N 6.54571 -6.43131 0.0 0
M  V30 20 C 7.28367 -7.01054 0.0 0
M  V30 21 C 5.0119 -2.87292 0.0 0
M  V30 22 C 8.51405 -2.9837 0.0 0
M  V30 23 C 8.29876 -6.63698 0.0 0
M  V30 24 C 4.79605 -6.58792 0.0 0
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M  V30 26 C 9.27269 -2.33219 0.0 0
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M  V30 28 C 4.03772 -7.2398 0.0 0
M V30 29 C 3.59147 -8.91156 0.0 0
M  V30 30 C 4.29709 -8.20631 0.0 0
M V30 31 C 2.62446 -8.65315 0.0 0
M  V30 32 C 3.06684 -6.98035 0.0 0
M  V30 33 C 2.36426 -7.69206 0.0 0
M  V30 34 C 10.6863 -7.78151 0.0 0
M  V30 35 C 9.9811 -7.07589 0.0 0
M  V30 36 C 10.4279 -8.74852 0.0 0
M  V30 37 C 8.75513 -8.30614 0.0 0
M  V30 38 C 9.46685 -9.00872 0.0 0
M  V30 39 C 9.71894 -0.660424 0.0 0
M  V30 40 C 9.01332 -1.36567 0.0 0
M  V30 41 C 10.6859 -0.918838 0.0 0
M  V30 42 C 10.2436 -2.59164 0.0 0
M  V30 43 C 10.9461 -1.87993 0.0 0
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M  V30 45 C 3.35713 -2.40682 0.0 0
M  V30 46 C 2.91029 -0.734192 0.0 0
M  V30 47 C 4.58309 -1.17657 0.0 0
M  V30 48 C 3.87138 -0.473995 0.0 0
M  V30 49 N 2.20203 -0.0282408 0.0 0 CHG=1
M  V30 50 N 11.3919 -0.210578 0.0 0 CHG=1
M  V30 51 N 11.1362 -9.45447 0.0 0 CHG=1
M  V30 52 N 1.91851 -9.36141 0.0 0 CHG=1
M  V30 53 C 1.83427 0.838106 0.0 0
M  V30 54 C 1.23653 -0.288636 0.0 0
M  V30 55 C 2.94253 0.832155 0.0 0
M  V30 56 C 12.3582 -0.46782 0.0 0
M  V30 57 C 11.9565 0.604924 0.0 0
M  V30 58 C 10.8756 0.496664 0.0 0
M  V30 59 C 10.879 -10.4208 0.0 0
M  V30 60 C 12.1017 -9.19408 0.0 0
M  V30 61 C 11.8445 -10.1604 0.0 0
M  V30 62 C 1.00216 -10.0292 0.0 0
M  V30 63 C 2.17891 -10.3269 0.0 0
M  V30 64 C 1.05811 -8.89591 0.0 0
M  V30 65 Fe 6.65 -4.7 0.0 0
M  V30 END ATOM
M  V30 BEGIN BOND
M  V30 1 2 1 5
M  V30 2 2 2 3
M  V30 3 1 3 1
M  V30 4 1 4 2
M  V30 5 1 5 4
M  V30 6 1 6 10
M  V30 7 1 7 8
M  V30 8 1 8 6
M  V30 9 1 9 7
M  V30 10 2 10 9
M  V30 11 1 11 15
M  V30 12 1 12 13
M  V30 13 2 13 11
M  V30 14 2 14 12
M  V30 15 1 15 14
M  V30 16 1 16 20
M  V30 17 1 17 18
M  V30 18 2 18 16
M  V30 19 2 19 17
M  V30 20 1 20 19
M  V30 21 1 1 21
M  V30 22 2 21 6
M  V30 23 2 4 22
M  V30 24 1 22 11
M  V30 25 1 14 23
M  V30 26 2 23 20
M  V30 27 1 17 24
M  V30 28 2 24 7
M  V30 29 1 21 25
M  V30 30 1 22 26
M  V30 31 1 23 27
M  V30 32 1 24 28
M  V30 33 2 30 28
M  V30 34 2 31 29
M  V30 35 1 28 32
M  V30 36 1 29 30
M  V30 37 2 32 33
M  V30 38 1 33 31
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M  V30 40 2 36 34
M  V30 41 1 27 37
M  V30 42 1 34 35
M  V30 43 2 37 38
M  V30 44 1 38 36
M  V30 45 2 40 26
M  V30 46 2 41 39
M  V30 47 1 26 42
M  V30 48 1 39 40
M  V30 49 2 42 43
M  V30 50 1 43 41
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M  V30 52 2 46 44
M  V30 53 1 25 47
M  V30 54 1 44 45
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M  V30 60 1 31 52
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M  V30 72 1 52 64
M  V30 73 8 5 65
M  V30 74 8 8 65
M  V30 75 8 15 65
M  V30 76 8 19 65
M  V30 END BOND
M  V30 END CTAB
M  END
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M  V30 64 C 3.13494 -10.341 0.0 0
M  V30 64 C 3.13494 -10.341 0.0 0
M  V30 65 Fe 8.425 -5.075 0.0 0
M  V30 65 Fe 8.425 -5.075 0.0 0 CHG=3
M  V30 66 Cl 9.13211 -4.36789 0.0 0
M  V30 66 Cl 9.33211 -3.94289 0.0 0 CHG=-1
M  V30 67 Cl 13.05 -8.875 0.0 0 CHG=-1
M  V30 67 Cl 13.95 -7.55 0.0 0 CHG=-1
M  V30 68 Cl 3.9 -8.8 0.0 0 CHG=-1
M  V30 68 Cl 2.875 -7.65 0.0 0 CHG=-1
M  V30 69 Cl 3.8 -1.35 0.0 0 CHG=-1
M  V30 69 Cl 2.975 -2.325 0.0 0 CHG=-1
M  V30 70 Cl 12.975 -1.225 0.0 0 CHG=-1
M  V30 70 Cl 13.8 -2.275 0.0 0 CHG=-1
M  V30 END ATOM
M  V30 END ATOM
M  V30 BEGIN BOND
M  V30 BEGIN BOND
Line 317: Line 178:
</chemform>
</chemform>


=== Photosensitizers===
==== Photosensitizers ====
<chemform smiles="C1C=CC2N(C3C=C4C=CC=CC4=CC=3)C3C=CC=CC=3N(C3C=C4C=CC=CC4=CC=3)C=2C=1" inchi="1S/C32H22N2/c1-3-11-25-21-27(19-17-23(25)9-1)33-29-13-5-7-15-31(29)34(32-16-8-6-14-30(32)33)28-20-18-24-10-2-4-12-26(24)22-28/h1-22H" inchikey="HPIOBCHPZVAATK-UHFFFAOYSA-N" height="200px" width="300px" float="none">
<chemform smiles="C1C=CC2N(C3C=C4C=CC=CC4=CC=3)C3C=CC=CC=3N(C3C=C4C=CC=CC4=CC=3)C=2C=1" inchi="1S/C32H22N2/c1-3-11-25-21-27(19-17-23(25)9-1)33-29-13-5-7-15-31(29)34(32-16-8-6-14-30(32)33)28-20-18-24-10-2-4-12-26(24)22-28/h1-22H" inchikey="HPIOBCHPZVAATK-UHFFFAOYSA-N" height="200px" width="300px" float="none">
   -INDIGO-11092309282D
   -INDIGO-11092309282D
Line 522: Line 383:
</chemform>
</chemform>


=== Investigations ===
==== Investigations ====
{{#experimentlist:|form=Photocatalytic_CO2_conversion_experiments|name=Table 1}}
{{#experimentlist: |form=Photocatalytic_CO2_conversion_experiments|name=Photocatalytic reduction of CO2}}
 
===Sacrificial Electron Donor ===
<chemform smiles="N(C(C)C)(C(C)C)CC" inchi="1S/C8H19N/c1-6-9(7(2)3)8(4)5/h7-8H,6H2,1-5H3" inchikey="JGFZNNIVVJXRND-UHFFFAOYSA-N" height="100px" width="150px" float="none">
  -INDIGO-12132211432D


  0  0  0  0  0  0  0  0  0  0  0 V3000
{{#experimentlist:|form=Photocatalytic_CO2_conversion_experiments|name=Photocatalytic reduction of CO|importFile=}}
M  V30 BEGIN CTAB
M  V30 COUNTS 9 8 0 0 0
M  V30 BEGIN ATOM
M  V30 1 N 10.1998 -5.92554 0.0 0
M  V30 2 C 10.4587 -6.89118 0.0 0
M  V30 3 C 9.75188 -7.59828 0.0 0
M  V30 4 C 9.23403 -5.66667 0.0 0
M  V30 5 C 8.97539 -4.70042 0.0 0
M  V30 6 C 8.5271 -6.37351 0.0 0
M  V30 7 C 10.9071 -5.21832 0.0 0
M  V30 8 C 11.8733 -5.47693 0.0 0
M  V30 9 C 10.6485 -4.25212 0.0 0
M  V30 END ATOM
M  V30 BEGIN BOND
M  V30 1 1 1 2
M  V30 2 1 2 3
M  V30 3 1 1 4
M  V30 4 1 4 5
M  V30 5 1 4 6
M  V30 6 1 1 7
M  V30 7 1 7 8
M  V30 8 1 7 9
M  V30 END BOND
M  V30 END CTAB
M  END
</chemform>
{{#moleculelink:|link=ZMANZCXQSJIPKH-UHFFFAOYSA-N|image=true}}
{{#moleculelink:|link=GSEJCLTVZPLZKY-UHFFFAOYSA-N|image=true}}
{{#moleculelink:|link=VDFIVJSRRJXMAU-UHFFFAOYSA-N|image=true}}
===Additives===
<chemform smiles="O([H])[H]" inchi="1S/H2O/h1H2" inchikey="XLYOFNOQVPJJNP-UHFFFAOYSA-N" height="50px" width="75px" float="none">
  -INDIGO-12132211442D
 
  0  0  0  0  0  0  0  0  0  0  0 V3000
M  V30 BEGIN CTAB
M  V30 COUNTS 3 2 0 0 0
M  V30 BEGIN ATOM
M  V30 1 O 9.58594 -4.36472 0.0 0
M  V30 2 H 8.66144 -4.74728 0.0 0
M  V30 3 H 10.3792 -4.97276 0.0 0
M  V30 END ATOM
M  V30 BEGIN BOND
M  V30 1 1 1 2
M  V30 2 1 1 3
M  V30 END BOND
M  V30 END CTAB
M  END
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  -INDIGO-12132211452D


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==== Sacrificial Electron Donor ====
M  V30 BEGIN CTAB
In this study, the experiments were done with the sacrificial electron donors DIPEA ({{#moleculelink:|link=JGFZNNIVVJXRND-UHFFFAOYSA-N|image=false|width=300|height=200}}), TEOA ({{#moleculelink:|link=GSEJCLTVZPLZKY-UHFFFAOYSA-N|image=false|width=300|height=200}}), BIH ({{#moleculelink:|link=VDFIVJSRRJXMAU-UHFFFAOYSA-N|image=false|width=300|height=200}}), and TEA ({{#moleculelink: |link=ZMANZCXQSJIPKH-UHFFFAOYSA-N|image=false|width=300|height=200}}).
M  V30 COUNTS 7 7 0 0 0
M  V30 BEGIN ATOM
M  V30 1 C 8.20985 -3.70007 0.0 0
M  V30 2 C 9.94015 -3.69959 0.0 0
M  V30 3 C 9.07664 -3.19997 0.0 0
M  V30 4 C 9.94015 -4.70053 0.0 0
M  V30 5 C 8.20985 -4.70502 0.0 0
M  V30 6 C 9.07882 -5.20003 0.0 0
M  V30 7 O 9.07725 -2.19997 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 3 7
M  V30 END BOND
M  V30 END CTAB
M  END
</chemform><chemform smiles="C(C(F)(F)F)O" inchi="1S/C2H3F3O/c3-2(4,5)1-6/h6H,1H2" inchikey="RHQDFWAXVIIEBN-UHFFFAOYSA-N" height="50px" width="75px" float="none">
  -INDIGO-12132211472D


  0  0  0  0  0  0  0  0  0  0  0 V3000
==== Additives ====
M  V30 BEGIN CTAB
In this study, different additives were used. As depicted in the investigation table, water ({{#moleculelink:|link=XLYOFNOQVPJJNP-UHFFFAOYSA-N|image=false|width=300|height=200}},) phenol ({{#moleculelink:|link=ISWSIDIOOBJBQZ-UHFFFAOYSA-N|image=false|width=300|height=200}}), and trifluoroethanol ({{#moleculelink:|link=RHQDFWAXVIIEBN-UHFFFAOYSA-N|image=false|width=300|height=200}}) were used.  
M  V30 COUNTS 6 5 0 0 0
[[Category:Photocatalytic CO2 conversion to CH4]][[Category:Publication]]
M  V30 BEGIN ATOM
M  V30 1 C 6.82192 -5.03421 0.0 0
M  V30 2 O 7.81584 -5.20252 0.0 0
M  V30 3 C 6.18635 -5.79969 0.0 0
M  V30 4 F 5.41792 -5.15324 0.0 0
M  V30 5 F 5.55273 -6.56115 0.0 0
M  V30 6 F 6.96078 -6.43583 0.0 0
M  V30 END ATOM
M  V30 BEGIN BOND
M  V30 1 1 1 2
M  V30 2 1 1 3
M  V30 3 1 3 4
M  V30 4 1 3 5
M  V30 5 1 3 6
M  V30 END BOND
M  V30 END CTAB
M  END
</chemform>
[[Category:Photocatalytic CO2 conversion to CH4]]

Latest revision as of 14:33, 16 August 2024


Abstract[edit | edit source]

Summary[edit | edit source]

A photochemical reduction of CO2 to CO and CH4 was shown using the iron porphyrin catalyst Fe(pTMAPP)Cl5 in combination with the phenoxazine photosensitizers 5,10-Di(2-naphthyl)-5,10-dihydrophenazine and 3,7-Di((1,1'-biphenyl)-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine. Turnover numbers (TONs) up to 149 for CO and 29 for CH4 were reached. The experiments were conducted under visible-light irradiation (λ > 435 nm) with a tertiary amine (see section SEDs below) as sacrificial electron donor.

Advances and special progress[edit | edit source]

This article contains the first demonstration for the reduction of CO2 to CH4 (complete 8e–/8H+ reduction) by a combination of an earth-abundant metal catalyst and an organic dye. So far, similar systems were shown to induce 2e–/2H+ reduction of CO2 to CO or formic acid.

Additional remarks[edit | edit source]

Methane was produced continuously (even after irradiation up to 4 days). The 8e–/8H+ reduction efficiency strongly depends on the redox properties of the organic photosensitizer and acidity of the proton source. In additional experiments, CO was used as the gas resource. The system consisting of iron porphyrin catalyst Fe(pTMAPP)Cl5 in combination with the phenoxazine photosensitizer 3,7-Di((1,1'-biphenyl)-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine was able to produce CH4 with a TON of 80 (85% selectivity, quantum yield: 0.47%).

Content of the published article in detail[edit | edit source]

The article contains results for the reduction of CO2 and CO as feedstock gases. The catalytic system performs best (referring to the TON of CH4 production) for CO as a feedstock.

Catalysts[edit | edit source]

Fe(pTMAPP)Cl5

Photosensitizers[edit | edit source]

5,10-Di(2-naphthyl)-5,10-dihydrophenazine 3,7-Di((1,1'-biphenyl)-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine

Investigations[edit | edit source]

catcat conc [µM]PSPS conc [mM]e-De-D conc [M]solvent Aadditives..λexc [nm].TON COTON CH4TON H2.
1.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEA

0.1

DMF

> 4355088
2.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEA

0.1

DMF

TFE> 435711410
3.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEA

0.1

DMF

TFE> 4351402923
Investigation-Name: Photocatalytic reduction of CO2
catcat conc [µM]PSPS conc [mM]e-De-D conc [M]solvent Aadditives..λexc [nm].TON CH4TON H2.
1.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEA

0.1

DMF

Visible light (>435)1021
2.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEA

0.1

DMF

TFEVisible light (>435)457
3.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEOA

0.1

DMF

TFEVisible light (>435)219
4.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

DIPEA

0.1

DMF

TFEVisible light (>435)397
5.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

BIH

0.1

DMF

TFEVisible light (>435)468
6.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEA

0.1

DMF

TFEVisible light (>435)8014
7.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEA

0.1

DMF

TFEVisible light (>435)2717
8.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEA

0.1

DMF

TFEVisible light (>435)1737
9.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEA

0.1

DMF

waterVisible light (>435)105
10.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEA

0.1

DMF

waterVisible light (>435)126
11.

Fe(pTMAPP)Cl5

0.01

Molecule:100493

1

TEA

0.1

DMF

PhOHVisible light (>435)2644
Investigation-Name: Photocatalytic reduction of CO

Sacrificial Electron Donor[edit | edit source]

In this study, the experiments were done with the sacrificial electron donors DIPEA (DIPEA), TEOA (TEOA), BIH (BIH), and TEA (TEA).

Additives[edit | edit source]

In this study, different additives were used. As depicted in the investigation table, water (H2O,) phenol (PhOH), and trifluoroethanol (TFE) were used.

Investigations

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