Cyclic Triindoles and Tetraindoles: Substituent and Symmetry Effects on their Structural and Electronic Characteristics
Ruiz-Delgado, María del Carmen,Ruiz, Constanza,López-Navarrete, Juan Teodomiro,Gómez-Lor, Berta
- Published
- 2016-10-07
- Language
- sp
Abstract
During the last decade heptacyclic 10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole (triindole) has been extensively studied as a new π-conjugated platform in the construction of self-assembling materials for optoelectronics. Specially remarkably is the record hole mobility values determined on triindole liquid crystals.1 In order to facilitate the design of new materials on a molecular basis and establish clear guidelines to fine tuning electronic parameters, we have recently synthesized new triindole and tetraindole-based systems.2-3 Our joint experimental and theoretical investigation shows that N-substitution, symmetry lowering of the platform, and insertion of π-spacers in extended dimers strongly impact on the fundamental electronic properties of triindoles.2 In addition, saddle-shaped tetraindoles are found to be an interesting 3D rigid scaffold to obtain electroactive molecules with increased dimensionality.3 We hope that this study can not only advance useful structure-property relationships of conjugated indole-based systems but also guide the design of new materials with potential applications in organic electronics.References 1. E.M. García-Frutos, U.K. Pandey, R. Termine, A. Omenat, J. Barberá, J.L. Serrano, A. Golemme, B. Gómez-Lor, Angew. Chem. Int. Ed. 2011, 50, 7399 2. a) C. Ruiz, J.T. López Navarrete, M.C.Ruiz Delgado, B. Gómez-Lor, Org. Lett. 2015, 17, 2258−2261. b) C. Ruiz, E.M. García-Frutos, D.A. da Silva Filho, J.T. López Navarrete, M.C. Ruiz Delgado, and B. Gómez-Lor, J. Phys. Chem. C 2014, 118, 5470−5477 3. C. Ruiz, A. Monge, E. Gutiérrez-Puebla, I. Alkorta, J. Elguero, J. T. López Navarrete, M.C. Ruiz Delgado and B. Gómez-Lor, submitted
Full text
Zing | Abstracts | Submission Cyclic Triindoles and Tetraindoles: Substituent and Symmetry Effects on their Structural and Electronic Characteristics M. Carmen Ruiz Delgado,a Constanza Ruiz,b Juan T. López Navarretea and Berta Gómez-Lora a, Department of Physical Chemistry, University of Málaga, 29071 Málaga, Spain b, Instituto de Ciencia de Materiales de Madrid, CSIC, Cantoblanco 28049, Madrid, Spain During the last decade heptacyclic 10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole (triindole) has been extensively studied as a new π-conjugated platform in the construction of self-assembling materials for optoelectronics. Specially remarkably is the record hole mobility values determined on triindole liquid crystals.1 In order to facilitate the design of new materials on a molecular basis and establish clear guidelines to fine tuning electronic parameters, we have recently synthesized new triindole and tetraindole-based systems.2-3 Our joint experimental and theoretical investigation shows that N-substitution, symmetry lowering of the platform, and insertion of π-spacers in extended dimers strongly impact on the fundamental electronic properties of triindoles.2 In addition, saddle-shaped tetraindoles are found to be an interesting 3D rigid scaffold to obtain electroactive molecules with increased dimensionality.3 We hope that this study can not only advance useful structure-property relationships of conjugated indole-based systems but also guide the design of new materials with potential applications in organic electronics. Figure 1. Cyclic triindoles and tetraindoles under study. References 1. E.M. García-Frutos, U.K. Pandey, R. Termine, A. Omenat, J. Barberá, J.L. Serrano, A. Golemme, B. Gómez-Lor, Angew. Chem. Int. Ed. 2011, 50, 7399 2. a) C. Ruiz, J.T. López Navarrete, M.C.Ruiz Delgado, B. Gómez-Lor, Org. Lett. 2015, 17, 2258−2261. b) C. Ruiz, E.M. García-Frutos, D.A. da Silva Filho, J.T. López Navarrete, M.C. Ruiz Delgado, and B. Gómez-Lor, J. Phys. Chem. C 2014, 118, 5470−5477 3. C. Ruiz, A. Monge, E. Gutiérrez-Puebla, I. Alkorta, J. Elguero, J. T. López Navarrete, M.C. Ruiz Delgado and B. Gómez-Lor, submitted www.zingconferences.com 1
