On-Surface Synthesis of Chiral π-Conjugate Porphyrin Tapes by Substrate-Regulated Dehydrogenative Coupling

Xiang F, Lu Y, Wang Z, Ju H, di Filippo G, Li C, Liu X, Leng X, Zhu J, Wang L, Schneider MA (2019)

Publication Type: Journal article, Original article

Publication year: 2019

Journal

Journal of Physical Chemistry C American Chemical Society

Book Volume: 123

Pages Range: 23007-23013

Issue: 37

Journal Issue: 37

DOI: 10.1021/acs.jpcc.9b06025

Abstract

On-surface enantioselective covalent coupling of nonfunctionalized porphyrins is demonstrated without utilizing chirality transfer from a self-assembled enantiopure precursor structure. We achieved to synthesize chiral porphyrin tapes on the Ag(110) surface by thermally induced dehydrogenative coupling using 5,15-diphenylporphyrin (2H-DPP) as a precursor. We employ scanning tunneling microscopy (STM), X-ray photoelectron spectroscopy (XPS), and density functional theory (DFT) to study the properties of the precursor molecules and resulting covalently bonded structures. Our analysis shows that the enantioselectivity is due to the specific molecule substrate interaction confining the orientation of the diffusing molecules and steric hindrance making non-enantiopure bonds energetically unfavorable.

Authors with CRIS profile

Feifei Xiang Professur für Experimentalphysik Gianluca di Filippo Lehrstuhl für Festkörperphysik Alexander Schneider Professur für Experimentalphysik

Involved external institutions

Nanchang University (NCU) / 南昌大学 CN China (CN) University of Science and Technology of China (USTC) CN China (CN)

How to cite

APA:

Xiang, F., Lu, Y., Wang, Z., Ju, H., di Filippo, G., Li, C.,... Schneider, M.A. (2019). On-Surface Synthesis of Chiral π-Conjugate Porphyrin Tapes by Substrate-Regulated Dehydrogenative Coupling. Journal of Physical Chemistry C, 123(37), 23007-23013. https://dx.doi.org/10.1021/acs.jpcc.9b06025

MLA:

Xiang, Feifei, et al. "On-Surface Synthesis of Chiral π-Conjugate Porphyrin Tapes by Substrate-Regulated Dehydrogenative Coupling." Journal of Physical Chemistry C 123.37 (2019): 23007-23013.

BibTeX: Download