Section of Chemistry

Ottosson Group

Quantum chemistry guided molecular design

Research in the Ottosson group is a blend of organic chemistry, theoretical chemistry and physical chemistry in rather equal proportions with an additional component of inorganic chemistry. Our general focus is on molecules (and materials) with intriguing electronic structures, and the research can be described as quantum chemistry guided molecular design, stretching from theory to synthesis and subsequent experimental studies as shown below. The projects fall into the research areas of organic photochemistry with focus on excited state aromaticity and antiaromaticity, novel conjugation phenomena, organosilicon chemistry, and molecular electronics.

We perform both experimental and computational studies, and have extensive collaborations with groups in physical and theoretical chemistry, physics and nanoengineering. We are “fundamentalists” as we view basic research and the development of new knowledge and new concepts as imperative for the future progress of our society. Yet, we are also concerned with the transfer of this new basic knowledge and the new concepts to more applied areas such as organic electronics and drug discovery.

Our research THEMES

  • Excited state aromaticity and antiaromaticity effects (Baird's rule): Pioneering the usage of Baird’s rule on excited state (anti)aromaticity for (i) the rationalization of a range of photophysical and photochemical properties and processes, (ii) the design of new optically and photochemically active compounds, and (iii) the development of new photochemical reactions. Recent key publications:

    • Impact of Ground and Excited State Aromaticity on Silole and Cyclopentadiene Excitation Energies and Excited State Polarities, K. Jorner, R. Emanuelsson, C. Dahlstrand, H. Tong, A. V. Denisova, H. Ottosson, Chem. Eur. J. 2014, 20, 9295 – 9303.

    • Excited State Aromaticity and Antiaromaticity: Opportunities for Photophysical and Photochemical Rationalization, M. Rosenberg, C. Dahlstrand, K. Kilså, H. Ottosson, Chem. Rev. 2014, 114, 5379 – 5425.

    • Exciting Excited-State Aromaticity, H. Ottosson, Nat. Chem., 2012, 4, 969-971 (a News & Views article)

  • Novel conjugation phenomena: Design and synthesis of compounds that display new forms of conjugation, incorporating heavier group 14 elements such as silicon and germanium into the organic framework. Present focus is on merging the cross-conjugation and hyperconjugation concepts.

    • 1,4-Disilacyclohexa-2,5-diene: A Cyclic Molecular Building Block that Allows for Remarkably Strong Neutral Cross-Hyper-conjugation, J. Tibbelin, A. Wallner, R. Emanuelsson, F. Heikenskjöld, M. Rosenberg, K. Yamazaki, D. Nauroozi, L. Karlsson, R. Feifel, R. Pettersson, J. Baumgartner, S. Ott, H. Ottosson, Chem. Sci. 2014, 5, 360 - 371.

    • Charge Transfer Through Cross-Hyperconjugated versus Cross-pi-Conjugated Bridges: An Intervalence Charge Transfer Study, E. Göransson, R. Emanuelsson, K. Jorner, T. F. Markle, L.Hammarström, H. Ottosson, Chem. Sci. 2013, 4, 3522 - 3532.

    • Cross-Hyperconjugation: An Unexplored Orbital Interaction between pi-Conjugated and Saturated Molecular Fragments, R. Emanuelsson, A. Wallner, E. A. M. Ng, J. R. Smith, D. Nauroozi, S. Ott, H. Ottosson, Angew. Chem. Int. Ed., 2013, 52, 983 – 987.

  • Structure and reactivity of Si=C bonded compounds: Development of the organic chemistry of Si=C double bonded compounds for selective (target-directed) organic synthesis, in particular developing the Diels-Alder reaction with silenes. Recent key publications:

    • The First Intramolecular Silene Diels-Alder Reactions, M. Czyzewski, J. D. Sellars, T. Guliashvili, J. Tibbelin, L. Johnstone, J. Bower, M. Box, H. Ottosson, P. G. Steel, Chem. Commun. 2014, 50, 2919 - 2921.

    • A Computational Investigation of Brook-type Silabenzenes and Their Possible Formation through [1,3]-Si→O Silyl Shifts, A. M. Rouf, B. O. Jahn, H. Ottosson, Organometallics, 2013, 32, 16 – 28.

    • Silenes: Connectors Between Classical Alkenes and Non-Classical Heavy Alkenes, H. Ottosson, A. M. Eklöf, Coord. Chem. Rev. 2008, 252, 1287 – 1314.

  • Molecular electronics: Design and synthesis of organosilicon compounds with targeted properties for applications in single-molecule electronics.

    • The Dicyanopentafulvene Core: A Template for the Design of Electron Acceptor Compounds, A. D. Finke, B. O. Jahn, A. Saithalavi, D. Nauroozi, S. Haberland, E. Mijangos, J.-P. Gisselbrecht, C. Boudon, W. B. Schweizer, S. Ott, H. Ottosson, F. Diederich, Chem. – Eur. J. 2015, accepted.

    • Configuration- and Conformation-Dependent Electronic Structure Variations in 1,4-Disubstituted Cyclohexanes Enabled by a Carbon-to-Silicon Exchange, R. Emanuelsson, H. Löfås, A. Wallner, D.Nauroozi, J. Baumgartner, C. Marschner, R. Ahuja, S. Ott, A. Grigoriev, H. Ottosson, Chem. Eur. J. 2014, 20, 9304 – 9311.

    • In Search of Flexible Molecular Wires with Near Conformer-Independent Conjugation and Conductance: A Computational Study,  R. Emanuelsson, H. Löfås, J. Zhu, R. Ahuja, A. Grigoriev, H. Ottosson, J. Phys. Chem. C, 2014, 118, 5637 - 5349.