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Synthesis of trans-A(2)B(2)- and trans-A(2)BC-Porphyrins with Polar 4 '-(Dimethylamino)tolan-4-yl Substituents, and a Screening Protocol for Vapor-Phase Deposition on Metal Surfaces

Alberti, M. N. and Nowakowska, S. and Tzirakis, M. D. and Nowakowski, J. and Fesser, P. and Schweizer, W. B. and Shchyrba, A. and Thilgen, C. and Jung, T. A. and Diederich, F.. (2014) Synthesis of trans-A(2)B(2)- and trans-A(2)BC-Porphyrins with Polar 4 '-(Dimethylamino)tolan-4-yl Substituents, and a Screening Protocol for Vapor-Phase Deposition on Metal Surfaces. European Journal of Organic Chemistry (26). pp. 5705-5719.

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Abstract

The role of polar 4-[p-(dimethylamino) phenylethynyl] phenyl substituents, with a calculated dipole moment of 3.35 Debye, in the self-assembly of trans-A(2)B(2)- and A(2)BC-substituted porphyrins was explored in the solid state by X-ray crystallography, and on an Au(111) surface by scanning tunneling microscopy (STM). Our results demonstrate that the dipolar character of these substituents blocks the 2D self-assembly of porphyrins into larger ordered domains on Au(111) at low coverage, whereas antiparallel dipole-dipole interactions govern the molecular ordering in the crystal. The STM analysis revealed an adaptation of the conformation of the prochiral building blocks and a site-selectivity of the adsorption. We present a general protocol for testing the suitability of higher-molecular-weight compounds, such as porphyrins, to be deposited on surface by sublimation in ultra-high vacuum (UHV). This protocol combines classical methods of chemical analysis with typical surface science techniques.
Faculties and Departments:05 Faculty of Science > Departement Physik > Physik
05 Faculty of Science > Departement Physik > Physik > Nanomechanik (Meyer)
UniBasel Contributors:Jung, Thomas A.
Item Type:Article, refereed
Publisher:Wiley
ISSN:1434-193X
e-ISSN:1099-0690
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:18 Sep 2017 10:38
Deposited On:01 Nov 2016 15:19

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