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Metal-free photoche...
Metal-free photochemical silylations and transfer hydrogenations of benzenoid hydrocarbons and graphene
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- Papadakis, Raffaello (author)
- Uppsala universitet,Molekylär biomimetik,Institutionen för kemi - BMC,Institutionen för kemi - Ångström
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- Li, Hu (author)
- Uppsala universitet,Tillämpad materialvetenskap,Electron microscopy and Nanoengineering
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- Bergman, J. (author)
- AstraZeneca R&D, Med Chem KH471, S-43183 Molndal, Sweden.
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- Lundstedt, Anna (author)
- Uppsala universitet,Organisk kemi,Institutionen för kemi - BMC
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- Jorner, Kjell (author)
- Uppsala universitet,Molekylär biomimetik,Institutionen för kemi - BMC,Institutionen för kemi - Ångström
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- Ayub, Rabia (author)
- Uppsala universitet,Molekylär biomimetik,Institutionen för kemi - BMC,Institutionen för kemi - Ångström,Henrik Ottosson
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- Haldar, Soumyajyoti (author)
- Uppsala universitet,Materialteori
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- Jahn, B. O. (author)
- Uppsala universitet,Institutionen för kemi - BMC
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- Denisova, Aleksandra (author)
- Uppsala universitet,Molekylär biomimetik,Institutionen för kemi - BMC,Institutionen för kemi - Ångström
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- Zietz, Burkhard (author)
- Uppsala universitet,Molekylär biomimetik,Institutionen för kemi - Ångström
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- Lindh, Roland (author)
- Uppsala universitet,Molekylär biomimetik,Teoretisk kemi
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- Sanyal, Biplab (author)
- Uppsala universitet,Materialteori
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- Grennberg, Helena (author)
- Uppsala universitet,Organisk kemi,Institutionen för kemi - BMC
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- Leifer, Klaus (author)
- Uppsala universitet,Tillämpad materialvetenskap
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- Ottosson, Henrik (author)
- Uppsala universitet,Molekylär biomimetik,Institutionen för kemi - BMC,Institutionen för kemi - Ångström,uppsala university
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(creator_code:org_t)
- 2016-10-06
- 2016
- English.
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In: Nature Communications. - : Nature Publishing Group. - 2041-1723. ; 7
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Abstract
Subject headings
Close
- The first hydrogenation step of benzene, which is endergonic in the electronic ground state (S 0), becomes exergonic in the first triplet state (T 1). This is in line with Baird's rule, which tells that benzene is antiaromatic and destabilized in its T 1 state and also in its first singlet excited state (S 1), opposite to S 0, where it is aromatic and remarkably unreactive. Here we utilized this feature to show that benzene and several polycyclic aromatic hydrocarbons (PAHs) to various extents undergo metal-free photochemical (hydro)silylations and transfer-hydrogenations at mild conditions, with the highest yield for naphthalene (photosilylation: 21%). Quantum chemical computations reveal that T 1-state benzene is excellent at H-atom abstraction, while cyclooctatetraene, aromatic in the T 1 and S 1 states according to Baird's rule, is unreactive. Remarkably, also CVD-graphene on SiO 2 is efficiently transfer-photohydrogenated using formic acid/water mixtures together with white light or solar irradiation under metal-free conditions. © The Author(s) 2016.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
- TEKNIK OCH TEKNOLOGIER -- Kemiteknik (hsv//swe)
- ENGINEERING AND TECHNOLOGY -- Chemical Engineering (hsv//eng)
Keyword
- aromatic compound
- benzene
- formic acid
- graphene
- hydrogen
- naphthalene
- polycyclic aromatic hydrocarbon
- carbon
- hydrocarbon
- irradiation
- PAH
- photochemistry
- solar radiation
- Article
- geometry
- hydrogenation
- mathematical analysis
- mathematical computing
- photoreactivity
- quantum chemistry
- silylation
- white light
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Papadakis, Raffa ...
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Li, Hu
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Bergman, J.
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Lundstedt, Anna
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Jorner, Kjell
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Ayub, Rabia
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show more...
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Haldar, Soumyajy ...
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Jahn, B. O.
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Denisova, Aleksa ...
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Zietz, Burkhard
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Lindh, Roland
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Sanyal, Biplab
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Grennberg, Helen ...
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Leifer, Klaus
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Ottosson, Henrik
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show less...
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NATURAL SCIENCES
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and Chemical Science ...
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NATURAL SCIENCES
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and Chemical Science ...
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- ENGINEERING AND TECHNOLOGY
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ENGINEERING AND ...
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and Chemical Enginee ...
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Uppsala University