In-Flow Heterogeneous Triplet–Triplet Annihilation Upconversion

In-Flow Heterogeneous Triplet–Triplet Annihilation Upconversion

Photon upconversion based on triplet–triplet annihilation (TTA-UC) is an attractive wavelength conversion with increasing use in organic synthesis in the homogeneous phase; however, this technology has not performed with canonical solid catalysts yet. Herein, a BOPHY dye covalently anchored on silic...

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Published in:ACS Physical Chemistry Au Vol. 4; no. 3; pp. 242 - 246
Main Authors: Castellanos-Soriano, Jorge, Garnes-Portolés, Francisco, Jiménez, M. Consuelo, Leyva-Pérez, Antonio, Pérez-Ruiz, Raúl
Format: Journal Article
Language:English
Published: United States American Chemical Society 22-05-2024
Subjects:
TTA
continuous-flow
Heterogeneous
visible light
Mizoroki−Heck
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Abstract Photon upconversion based on triplet–triplet annihilation (TTA-UC) is an attractive wavelength conversion with increasing use in organic synthesis in the homogeneous phase; however, this technology has not performed with canonical solid catalysts yet. Herein, a BOPHY dye covalently anchored on silica is successfully used as a sensitizer in a TTA system that efficiently catalyzes Mizoroki–Heck coupling reactions. This procedure has enabled the implementation of in-flow reaction conditions for the synthesis of a variety of aromatic compounds, and mechanistic proof has been obtained by means of transient absorption spectroscopy.
AbstractList Photon upconversion based on triplet-triplet annihilation (TTA-UC) is an attractive wavelength conversion with increasing use in organic synthesis in the homogeneous phase; however, this technology has not performed with canonical solid catalysts yet. Herein, a BOPHY dye covalently anchored on silica is successfully used as a sensitizer in a TTA system that efficiently catalyzes Mizoroki-Heck coupling reactions. This procedure has enabled the implementation of in-flow reaction conditions for the synthesis of a variety of aromatic compounds, and mechanistic proof has been obtained by means of transient absorption spectroscopy.
Author Castellanos-Soriano, Jorge
Jiménez, M. Consuelo
Leyva-Pérez, Antonio
Garnes-Portolés, Francisco
Pérez-Ruiz, Raúl
AuthorAffiliation Instituto de Tecnología Química (ITQ)
Universitat Politècnica de València-Consejo Superior de Investigaciones Científicas (UPV-CSIC)
Departamento de Química
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  organization: Departamento de Química
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Cites_doi 10.1002/anie.201915762
10.1021/jacs.8b07884
10.1021/acscatal.0c01569
10.1016/j.ccr.2016.12.021
10.1038/s41586-018-0835-2
10.1039/D0QO00466A
10.1038/s41929-021-00592-3
10.1002/adsc.202101048
10.1007/s41061-022-00378-6
10.1021/jacs.3c02832
10.1016/j.apcata.2008.10.018
10.1021/jacs.7b05942
10.1002/anie.201303188
10.1021/ja00097a038
10.1021/acscatal.0c00801
10.1007/s43630-022-00203-5
10.1039/C8CC02169D
10.1039/D1CS00162K
10.1039/C5TC03193A
10.1039/D1TC03551G
10.1021/ja502477a
10.1021/acs.chemrev.1c00409
10.1021/jacsau.2c00265
10.1002/anie.202301506
10.1021/acs.chemrev.1c00332
10.1016/j.ccr.2018.02.011
10.1021/acs.chemrev.1c00603
10.1126/science.1258232
10.1021/jacs.0c06976
10.1002/adma.200901263
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continuous-flow
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visible light
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References ref9/cit9
ref6/cit6
ref3/cit3
ref27/cit27
ref18/cit18
ref11/cit11
ref25/cit25
ref16/cit16
ref29/cit29
ref23/cit23
ref14/cit14
ref8/cit8
ref5/cit5
ref2/cit2
ref28/cit28
ref20/cit20
ref17/cit17
ref10/cit10
ref26/cit26
ref19/cit19
ref21/cit21
ref12/cit12
ref15/cit15
ref22/cit22
ref13/cit13
ref4/cit4
ref30/cit30
ref1/cit1
ref24/cit24
ref7/cit7
References_xml – ident: ref1/cit1
  doi: 10.1002/anie.201915762
– ident: ref28/cit28
  doi: 10.1021/jacs.8b07884
– ident: ref24/cit24
  doi: 10.1021/acscatal.0c01569
– ident: ref25/cit25
  doi: 10.1016/j.ccr.2016.12.021
– ident: ref13/cit13
  doi: 10.1038/s41586-018-0835-2
– ident: ref3/cit3
  doi: 10.1039/D0QO00466A
– ident: ref23/cit23
  doi: 10.1038/s41929-021-00592-3
– ident: ref19/cit19
  doi: 10.1002/adsc.202101048
– ident: ref2/cit2
  doi: 10.1007/s41061-022-00378-6
– ident: ref5/cit5
  doi: 10.1021/jacs.3c02832
– ident: ref16/cit16
  doi: 10.1016/j.apcata.2008.10.018
– ident: ref17/cit17
  doi: 10.1021/jacs.7b05942
– ident: ref27/cit27
  doi: 10.1002/anie.201303188
– ident: ref30/cit30
  doi: 10.1021/ja00097a038
– ident: ref26/cit26
  doi: 10.1021/acscatal.0c00801
– ident: ref18/cit18
  doi: 10.1007/s43630-022-00203-5
– ident: ref15/cit15
  doi: 10.1039/C8CC02169D
– ident: ref9/cit9
  doi: 10.1039/D1CS00162K
– ident: ref29/cit29
  doi: 10.1039/C5TC03193A
– ident: ref11/cit11
  doi: 10.1039/D1TC03551G
– ident: ref22/cit22
  doi: 10.1021/ja502477a
– ident: ref8/cit8
  doi: 10.1021/acs.chemrev.1c00409
– ident: ref6/cit6
  doi: 10.1021/jacsau.2c00265
– ident: ref21/cit21
  doi: 10.1002/anie.202301506
– ident: ref14/cit14
  doi: 10.1021/acs.chemrev.1c00332
– ident: ref10/cit10
  doi: 10.1016/j.ccr.2018.02.011
– ident: ref7/cit7
  doi: 10.1021/acs.chemrev.1c00603
– ident: ref4/cit4
  doi: 10.1126/science.1258232
– ident: ref12/cit12
  doi: 10.1021/jacs.0c06976
– ident: ref20/cit20
  doi: 10.1002/adma.200901263
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Snippet Photon upconversion based on triplet–triplet annihilation (TTA-UC) is an attractive wavelength conversion with increasing use in organic synthesis in the...
Photon upconversion based on triplet-triplet annihilation (TTA-UC) is an attractive wavelength conversion with increasing use in organic synthesis in the...
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Title In-Flow Heterogeneous Triplet–Triplet Annihilation Upconversion
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