Editing Rhenium(I) trinuclear rings as highly efficient redox photosensitizers for photocatalytic CO2 reduction

{{FaultyMolecule}}{{BaseTemplate}}
{{DOI|doi=10.1039/c6sc01913g}}{{MissingInvestigation}} 
===Abstract===
==== Summary====
A photochemical reduction of CO<sub>2</sub> to CO or formic acid was shown using the bipyridine-based rhenium, ruthenium and manganese catalysts {{#moleculelink:|link=NZCMNMSVXYOMGS-UHFFFAOYSA-N|image=false|width=300|height=200}}, {{#moleculelink:|link=XUQJAKJUMNDNTK-UHFFFAOYSA-L|image=false|width=300|height=200}} or {{#moleculelink: |link=OMERWMHUIAGAOR-UHFFFAOYSA-N|image=false|width=300|height=200}} in combination with cyclic rhenium-based trinuclear redox photosensitizers. Turnover numbers (TONs) of  up to 290 for formic acid were reached in DMA with the ruthenium complex {{#moleculelink:|link=XUQJAKJUMNDNTK-UHFFFAOYSA-L|image=false|width=300|height=200}} and photosensitizer {{#moleculelink:|link=KSOIVZAANOLODS-UHFFFAOYSA-T|image=false|width=300|height=200}}. For CO production, TONs of up to 98 were obtained in DMF with the rhenium complex {{#moleculelink:|link=NZCMNMSVXYOMGS-UHFFFAOYSA-N|image=false|width=300|height=200}} and photosensitizer {{#moleculelink:|link=LOLRMPNEYKEGPF-UHFFFAOYSA-T|image=false|width=300|height=200}}. The experiments were conducted under visible-light irradiation (λ = 436 nm) using TEOA as sacrificial electron donor (see section SEDs below).
====Advances and special progress====
Re(I)-based trinuclear photosensitizers were developed and allowed for high product selectivities for CO or formic acid in CO<sub>2</sub> reduction attempts with different bipyridine-based catalysts.
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====Additional remarks====
===Content of the published article in detail===
The article contains results for the reduction of CO<sub>2</sub> to CO or formic acid under visible-light catalysis using bipyridine-based complexes and rhenium-based trinuclear rings as photosensitizers. The catalytic system performs best in DMA for formic acid production (referring to the TON of formic acid production) and in DMF for CO production.
==== Catalyst====
<chemform smiles="C1C=C2C3C=CC=CN=3[Re+]([C-]#[O+])([C-]#[O+])([C-]#[O+])(N#CC)N2=CC=1.[P-](F)(F)(F)(F)(F)F" inchi="1S/C10H8N2.C2H3N.3CO.F6P.Re/c1-3-7-11-9(5-1)10-6-2-4-8-12-10;1-2-3;3*1-2;1-7(2,3,4,5)6;/h1-8H;1H3;;;;;/q;;;;;-1;+1" inchikey="NZCMNMSVXYOMGS-UHFFFAOYSA-N" height="200px" width="300px" float="none">
  -INDIGO-07282314582D

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M  V30 COUNTS 29 30 0 0 0
M  V30 BEGIN ATOM
M  V30 1 C 4.65985 -3.35007 0.0 0
M  V30 2 C 6.39015 -3.34959 0.0 0
M  V30 3 C 5.52664 -2.84997 0.0 0
M  V30 4 N 6.39015 -4.35053 0.0 0
M  V30 5 C 4.65985 -4.35502 0.0 0
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M  V30 7 C 5.53268 -5.85003 0.0 0
M  V30 8 C 6.40503 -7.34433 0.0 0
M  V30 9 N 6.40144 -6.3467 0.0 0
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M  V30 11 C 4.66465 -6.35643 0.0 0
M  V30 12 C 4.67497 -7.35646 0.0 0
M  V30 13 Re 7.38118 -5.25053 0.0 0 CHG=1
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M  V30 15 C 8.2472 -4.75053 0.0 0 CHG=-1
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M  V30 17 C 7.38118 -6.25053 0.0 0 CHG=-1
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M  V30 19 O 9.11323 -6.25053 0.0 0 CHG=1
M  V30 20 O 7.38118 -7.25053 0.0 0 CHG=1
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M  V30 END ATOM
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M  V30 END BOND
M  V30 END CTAB
M  END
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  -INDIGO-01102416342D

  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 2 C 7.16515 -2.27459 0.0 0
M  V30 3 C 6.30164 -1.77497 0.0 0
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M  V30 11 C 5.43385 -5.27809 0.0 0
M  V30 12 C 5.44031 -6.27814 0.0 0
M  V30 13 Ru 8.325 -4.25 0.0 0 CHG=2
M  V30 14 C 4.57429 -6.77814 0.0 0
M  V30 15 C 3.70826 -7.27814 0.0 0
M  V30 16 C 9.28211 -3.26789 0.0 0 CHG=-1
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M  V30 24 C 4.06882 -2.6411 0.0 0
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M  V30 27 C 4.07429 -5.91211 0.0 0
M  V30 END ATOM
M  V30 BEGIN BOND
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M  V30 6 1 6 4
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M  V30 END BOND
M  V30 END CTAB
M  END
</chemform><chemform smiles="C(C(C)(C)C)1C=C2C3C=C(C(C)(C)C)C=CN=3[Mn+]([C-]#[O+])([C-]#[O+])([C-]#[O+])(N#CC)N2=CC=1.F[P-](F)(F)(F)(F)F" inchikey="OMERWMHUIAGAOR-UHFFFAOYSA-N" inchi="1S/C18H24N2.C2H3N.3CO.F6P.Mn/c1-17(2,3)13-7-9-19-15(11-13)16-12-14(8-10-20-16)18(4,5)6;1-2-3;3*1-2;1-7(2,3,4,5)6;/h7-12H,1-6H3;1H3;;;;;/q;;;;;-1;+1" float="none" width="200" height="200">
  -INDIGO-02192415212D

  0  0  0  0  0  0  0  0  0  0  0 V3000
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M  V30 BEGIN ATOM
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M  V30 3 F 12.6945 -5.18061 0.0 0
M  V30 4 F 13.5447 -4.67885 0.0 0
M  V30 5 F 12.6888 -3.2002 0.0 0
M  V30 6 F 13.541 -3.69224 0.0 0
M  V30 7 F 11.8296 -3.68535 0.0 0
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M  V30 14 C 6.13447 -6.61103 0.0 0
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M  V30 19 C 5.28061 -8.09733 0.0 0
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M  V30 22 C 4.42427 -8.59174 0.0 0
M  V30 23 C 3.56792 -9.08615 0.0 0
M  V30 24 Mn 8.13836 -6.06687 0.0 0 CHG=1
M  V30 25 N 8.13836 -5.07805 0.0 0
M  V30 26 C 8.9947 -5.57246 0.0 0 CHG=-1
M  V30 27 C 8.9947 -6.56128 0.0 0 CHG=-1
M  V30 28 C 8.39429 -7.02199 0.0 0 CHG=-1
M  V30 29 C 8.13836 -4.08923 0.0 0
M  V30 30 C 8.13836 -3.10041 0.0 0
M  V30 31 O 9.85105 -5.07805 0.0 0 CHG=1
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M  V30 33 O 8.65021 -7.97712 0.0 0 CHG=1
M  V30 34 C 4.41886 -2.64461 0.0 0
M  V30 35 C 3.55284 -4.14461 0.0 0
M  V30 36 C 4.42427 -9.59174 0.0 0
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M  V30 END ATOM
M  V30 BEGIN BOND
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M  V30 6 1 2 7
M  V30 7 2 10 8
M  V30 8 2 11 9
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M  V30 15 2 17 15
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M  V30 17 1 15 16
M  V30 18 2 18 19
M  V30 19 1 19 17
M  V30 20 1 8 20
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M  V30 35 1 20 34
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M  V30 END BOND
M  V30 END CTAB
M  END
</chemform>

====Photosensitizer ====
<chemform smiles="C1C=C2P(C3C=CC=CC=3)(C3C=CC=CC=3)~[Re+]3(N4=C(C5N3=CC([*])=C([*])C=5)C=C([*])C([*])=C4)([C-]#[O+])([C-]#[O+])~P(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC(P(C4C=CC=CC=4)(C4C=CC=CC=4)~[Re+]4(N5=C(C6N4=CC([*])=C([*])C=6)C=C([*])C([*])=C5)([C-]#[O+])([C-]#[O+])~P(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC(P(C5C=CC=CC=5)(C5C=CC=CC=5)~[Re+]5(N6=CC([*])=C([*])C=C6C6C=C([*])C([*])=CN=65)([C-]#[O+])([C-]#[O+])~P(C5C=CC=CC=5)(C5C=CC=CC=5)C=1C=C2)=CC=4)=CC=3" inchi="" inchikey="" height="200px" width="300px" float="none" r1="H,CH3,CH3,H" r2="CH3,H,CH3,OMe">
  -INDIGO-02192415292D

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M  V30 23 P 11.3412 -8.8526 0.0 0
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M  V30 26 Re 6.91477 -7.54207 0.0 0 CHG=1
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M  V30 127 C 7.63865 1.55414 0.0 0
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M  V30 135 C 11.6417 0.787854 0.0 0
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M  V30 137 C 11.2008 0.0195098 0.0 0
M  V30 138 R# 11.6407 2.32933 0.0 0 RGROUPS=(1 1)
M  V30 139 R# 7.19379 2.32467 0.0 0 RGROUPS=(1 1)
M  V30 140 C 4.8284 -10.9379 0.0 0
M  V30 141 C 3.49538 -11.708 0.0 0
M  V30 142 C 4.38299 -11.7088 0.0 0
M  V30 143 C 3.05009 -10.9367 0.0 0
M  V30 144 N 4.38134 -10.1636 0.0 0
M  V30 145 C 3.49156 -10.1687 0.0 0
M  V30 146 C 3.0467 -9.39818 0.0 0
M  V30 147 C 1.71272 -8.6297 0.0 0
M  V30 148 C 2.15633 -9.39851 0.0 0
M  V30 149 C 2.15749 -7.85815 0.0 0
M  V30 150 N 3.49324 -8.62354 0.0 0
M  V30 151 C 3.04337 -7.85585 0.0 0
M  V30 152 R# 0.822997 -8.6297 0.0 0 RGROUPS=(1 1)
M  V30 153 R# 3.05051 -12.4785 0.0 0 RGROUPS=(1 1)
M  V30 154 R# 4.82786 -12.4793 0.0 0 RGROUPS=(1 2)
M  V30 155 R# 1.71137 -7.08835 0.0 0 RGROUPS=(1 2)
M  V30 156 R# 14.1785 -12.4648 0.0 0 RGROUPS=(1 2)
M  V30 157 R# 17.2895 -7.07069 0.0 0 RGROUPS=(1 2)
M  V30 158 R# 6.3044 0.786395 0.0 0 RGROUPS=(1 2)
M  V30 159 R# 12.5314 0.789322 0.0 0 RGROUPS=(1 2)
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 2 9 7
M  V30 8 2 10 8
M  V30 9 1 7 11
M  V30 10 1 8 9
M  V30 11 2 11 12
M  V30 12 1 12 10
M  V30 13 2 15 13
M  V30 14 2 16 14
M  V30 15 1 13 17
M  V30 16 1 14 15
M  V30 17 2 17 18
M  V30 18 1 18 16
M  V30 19 1 3 19
M  V30 20 1 13 20
M  V30 21 1 6 21
M  V30 22 1 9 22
M  V30 23 1 12 23
M  V30 24 1 16 24
M  V30 25 8 19 27
M  V30 26 8 20 27
M  V30 27 8 21 26
M  V30 28 8 22 26
M  V30 29 8 23 25
M  V30 30 8 24 25
M  V30 31 10 25 28
M  V30 32 10 25 29
M  V30 33 10 27 30
M  V30 34 10 27 31
M  V30 35 10 26 32
M  V30 36 10 26 33
M  V30 37 3 33 34
M  V30 38 3 32 35
M  V30 39 3 28 36
M  V30 40 3 29 37
M  V30 41 3 30 38
M  V30 42 3 31 39
M  V30 43 1 24 40
M  V30 44 2 42 40
M  V30 45 2 43 41
M  V30 46 1 40 44
M  V30 47 1 41 42
M  V30 48 2 44 45
M  V30 49 1 45 43
M  V30 50 1 24 46
M  V30 51 2 48 46
M  V30 52 2 49 47
M  V30 53 1 46 50
M  V30 54 1 47 48
M  V30 55 2 50 51
M  V30 56 1 51 49
M  V30 57 1 20 52
M  V30 58 2 54 52
M  V30 59 2 55 53
M  V30 60 1 52 56
M  V30 61 1 53 54
M  V30 62 2 56 57
M  V30 63 1 57 55
M  V30 64 1 20 58
M  V30 65 2 60 58
M  V30 66 2 61 59
M  V30 67 1 58 62
M  V30 68 1 59 60
M  V30 69 2 62 63
M  V30 70 1 63 61
M  V30 71 1 19 64
M  V30 72 2 66 64
M  V30 73 2 67 65
M  V30 74 1 64 68
M  V30 75 1 65 66
M  V30 76 2 68 69
M  V30 77 1 69 67
M  V30 78 1 19 70
M  V30 79 2 72 70
M  V30 80 2 73 71
M  V30 81 1 70 74
M  V30 82 1 71 72
M  V30 83 2 74 75
M  V30 84 1 75 73
M  V30 85 1 23 76
M  V30 86 2 78 76
M  V30 87 2 79 77
M  V30 88 1 76 80
M  V30 89 1 77 78
M  V30 90 2 80 81
M  V30 91 1 81 79
M  V30 92 1 23 82
M  V30 93 2 84 82
M  V30 94 2 85 83
M  V30 95 1 82 86
M  V30 96 1 83 84
M  V30 97 2 86 87
M  V30 98 1 87 85
M  V30 99 1 22 88
M  V30 100 2 90 88
M  V30 101 2 91 89
M  V30 102 1 88 92
M  V30 103 1 89 90
M  V30 104 2 92 93
M  V30 105 1 93 91
M  V30 106 1 22 94
M  V30 107 2 96 94
M  V30 108 2 97 95
M  V30 109 1 94 98
M  V30 110 1 95 96
M  V30 111 2 98 99
M  V30 112 1 99 97
M  V30 113 1 21 100
M  V30 114 2 102 100
M  V30 115 2 103 101
M  V30 116 1 100 104
M  V30 117 1 101 102
M  V30 118 2 104 105
M  V30 119 1 105 103
M  V30 120 1 21 106
M  V30 121 2 108 106
M  V30 122 2 109 107
M  V30 123 1 106 110
M  V30 124 1 107 108
M  V30 125 2 110 111
M  V30 126 1 111 109
M  V30 127 2 114 112
M  V30 128 2 115 113
M  V30 129 1 112 116
M  V30 130 1 113 114
M  V30 131 2 116 117
M  V30 132 1 117 115
M  V30 133 1 117 118
M  V30 134 2 120 118
M  V30 135 2 121 119
M  V30 136 1 118 122
M  V30 137 1 119 120
M  V30 138 2 122 123
M  V30 139 1 123 121
M  V30 140 1 119 124
M  V30 141 1 113 125
M  V30 142 2 128 126
M  V30 143 2 129 127
M  V30 144 1 126 130
M  V30 145 1 127 128
M  V30 146 2 130 131
M  V30 147 1 131 129
M  V30 148 1 131 132
M  V30 149 2 134 132
M  V30 150 2 135 133
M  V30 151 1 132 136
M  V30 152 1 133 134
M  V30 153 2 136 137
M  V30 154 1 137 135
M  V30 155 1 133 138
M  V30 156 1 127 139
M  V30 157 2 142 140
M  V30 158 2 143 141
M  V30 159 1 140 144
M  V30 160 1 141 142
M  V30 161 2 144 145
M  V30 162 1 145 143
M  V30 163 1 145 146
M  V30 164 2 148 146
M  V30 165 2 149 147
M  V30 166 1 146 150
M  V30 167 1 147 148
M  V30 168 2 150 151
M  V30 169 1 151 149
M  V30 170 1 147 152
M  V30 171 1 141 153
M  V30 172 10 26 150
M  V30 173 10 26 144
M  V30 174 10 25 122
M  V30 175 10 25 116
M  V30 176 10 27 130
M  V30 177 10 27 136
M  V30 178 1 142 154
M  V30 179 1 149 155
M  V30 180 1 121 156
M  V30 181 1 114 157
M  V30 182 1 128 158
M  V30 183 1 135 159
M  V30 END BOND
M  V30 END CTAB
M  END
</chemform>

====Investigation====
{{#experimentlist:|form=Photocatalytic_CO2_conversion_experiments|name=Table 1}}{{#experimentlist:|form=Photocatalytic_CO2_conversion_experiments|name=Table 2}}
====Sacrificial Electron Donor ====
In this study, the experiments were done with the sacrificial electron donor TEOA ([[Molecule:100507|100507]]).
==== Additives====
In this study, no additives were tested.
[[Category:Photocatalytic CO2 conversion to HCOOH]]