Solution Versus On-Surface Synthesis of Peripherally Oxygen-Annulated Porphyrins through C-O Bond Formation

被引：0

作者：

Deyerling, Joel ^{[1
]}

Berna, Beatrice Berionni ^{[2
]}

Biloborodov, Dmytro ^{[3
]}

Haag, Felix ^{[1
]}

Toemekce, Sena ^{[1
]}

Cuxart, Marc G. ^{[1
]}

Li, Conghui ^{[1
]}

Auwaerter, Willi ^{[1
]}

Bonifazi, Davide ^{[2
]}

机构：

[1] Tech Univ Munich, TUM Sch Nat Sci, Phys Dept E20, D-85748 Garching, Germany

[2] Univ Vienna, Inst Organ Chem, Fac Chem, A-1090 Vienna, Austria

[3] Univ Namur, Dept Chem, Rue Bruxelles 61, B-5000 Namur, Belgium

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2025年 / 64卷 / 01期

基金：

欧盟地平线“2020”;

关键词：

porphyrin; on-surface synthesis; non-contact atomic force microscopy; C-O bond formation; O-annulation; MOLECULAR WIRES; TAPES; OXIDE;

D O I：

10.1002/anie.202412978

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This study investigates the synthesis of tetra- and octa-O-fused porphyrinoids employing an oxidative O-annulation approach through C-H activation. Despite encountering challenges such as overoxidation and instability in conventional solution protocols, successful synthesis was achieved on Au(111) surfaces under ultra-high vacuum (UHV) conditions. X-ray photoelectron spectroscopy, scanning tunneling microscopy, and non-contact atomic force microscopy elucidated the preferential formation of pyran moieties via C-O bond formation and subsequent self-assembly driven by C-H & sdot;& sdot;& sdot;O interactions. Furthermore, the O-annulation process was found to reduce the HOMO-LUMO gap by lifting the HOMO energy level, with the effect rising upon increasing the number of embedded O-atoms.

引用

页数：8

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