Planar and curved π-extended porphyrins by on-surface cyclodehydrogenation

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68378271%3A_____%2F24%3A00637604" target="_blank" >RIV/68378271:_____/24:00637604 - isvavai.cz</a>

Výsledek na webu

<a href="https://hdl.handle.net/11104/0368624" target="_blank" >https://hdl.handle.net/11104/0368624</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/jacs.4c12460" target="_blank" >10.1021/jacs.4c12460</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Planar and curved π-extended porphyrins by on-surface cyclodehydrogenation

Popis výsledku v původním jazyce

Recent advancements in on-surface synthesis have enabled the reliable and predictable preparation of atomically precise low-dimensional materials with remarkable properties, which are often unattainable through traditional wet chemistry. Among these materials, porphyrins stand out as a particularly intriguing class of molecules, extensively studied both in solution and on surfaces. Their appeal lies in the ability to fine-tune their unique chemical and physical properties through central metal exchange or peripheral functionalization. However, the synthesis of π-extended porphyrins featuring unsubstituted anthracenyl groups has remained elusive. Herein, we report an in vacuo temperature-controlled cyclodehydrogenation of bis- and tetraanthracenyl Zn(II) porphyrins on a gold(111) surface. By gradually increasing the temperature, sequential dehydrogenation leads to the formation of fused anthracenyl porphyrin products. Notably, at high molecular coverage, the formation of bowl-shaped porphyrins occurs, along with transmetalation of Zn with Au. These findings open the door to a variety of π-extended anthracenyl-containing porphyrin products via cyclodehydrogenation and transmetalation, offering significant potential in the fields of molecular (photo/electro)catalysis, (opto)electronics, and spintronics.

Název v anglickém jazyce

Planar and curved π-extended porphyrins by on-surface cyclodehydrogenation

Popis výsledku anglicky

Recent advancements in on-surface synthesis have enabled the reliable and predictable preparation of atomically precise low-dimensional materials with remarkable properties, which are often unattainable through traditional wet chemistry. Among these materials, porphyrins stand out as a particularly intriguing class of molecules, extensively studied both in solution and on surfaces. Their appeal lies in the ability to fine-tune their unique chemical and physical properties through central metal exchange or peripheral functionalization. However, the synthesis of π-extended porphyrins featuring unsubstituted anthracenyl groups has remained elusive. Herein, we report an in vacuo temperature-controlled cyclodehydrogenation of bis- and tetraanthracenyl Zn(II) porphyrins on a gold(111) surface. By gradually increasing the temperature, sequential dehydrogenation leads to the formation of fused anthracenyl porphyrin products. Notably, at high molecular coverage, the formation of bowl-shaped porphyrins occurs, along with transmetalation of Zn with Au. These findings open the door to a variety of π-extended anthracenyl-containing porphyrin products via cyclodehydrogenation and transmetalation, offering significant potential in the fields of molecular (photo/electro)catalysis, (opto)electronics, and spintronics.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10302 - Condensed matter physics (including formerly solid state physics, supercond.)

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of the American Chemical Society

ISSN

0002-7863

e-ISSN

1520-5126

Svazek periodika

146

Číslo periodika v rámci svazku

50

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

9

Strana od-do

34600-34608

Kód UT WoS článku

001370310700001

EID výsledku v databázi Scopus

2-s2.0-85211095382