Core-modified rubyrins containing dithienylethene moieties.

Angew Chem Int Ed Engl

State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (China); Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578 (Japan).

Published: June 2014

Two stable core-modified rubyrins bearing one and two dithienylethene (DTE) units (1 and 2) have been synthesized. With one "closed-form" DTE unit, 1 shows aromaticity associated with its conjugated circuit of 26 π-electrons. In contrast, rubyrin 2 containing one "open-form" DTE unit has nonaromatic properties.

Download full-text PDF

Source
http://dx.doi.org/10.1002/anie.201402711DOI Listing

Publication Analysis

Top Keywords

core-modified rubyrins
8
dte unit
8
rubyrins dithienylethene
4
dithienylethene moieties
4
moieties stable
4
stable core-modified
4
rubyrins bearing
4
bearing dithienylethene
4
dithienylethene dte
4
dte units
4

Similar Publications

Solvent-Dependent Core-Modified Rubyrin Self-Assembly at Liquid/Solid Interfaces.

Langmuir

April 2020

CAS Key Laboratory of Standardization and Measurement for Nanotechnology, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology (NCNST), Beijing 100190, China.

Scanning tunneling microscopy (STM) was utilized to disclose four novel core-modified rubyrin self-assembly behaviors on the highly-oriented pyrolytic graphite (HOPG) surface, of which NS-OR(1)/NSe-OR(2) had no phenanthrene pyrrole ring and NS-OR(3)/NSe-OR(4) had phenanthrene-fused pyrrole rings and meso-aryl substituents. It was discovered that the core-modified rubyrin could self-assemble into either face-on or edge-on monolayer structures selectively at the liquid/HOPG interface in different solvents. There was an obvious solvent-dependent self-assembly for NS-OR(3)/NSe-OR(4), which adopted an edge-on and face-on structure in 1-phenyloctane and 1-heptanoic acid solvents, respectively, whereas NS-OR(1)/NSe-OR(2) showed no obvious difference in the assembly structure, which both adopted a face-on structure in the two solvents.

View Article and Find Full Text PDF

The synthesis, characterization, and photophysical and electrochemical properties of a novel tetrathiafulvalene (TTF)-annulated core-modified porphyrin (1) and its expanded rubyrin analogue (2) are described. The sulfur core modifications in 1 and 2 allow a feasible intramolecular charge transfer from the TTF fragments to the central conjugated core as inferred from comparative spectroscopic and electrochemical measurements. DFT calculations also support the intramolecular charge transfer nature of 1 and 2 upon excitation.

View Article and Find Full Text PDF

Core-modified rubyrins containing dithienylethene moieties.

Angew Chem Int Ed Engl

June 2014

State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 (China); Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578 (Japan).

Two stable core-modified rubyrins bearing one and two dithienylethene (DTE) units (1 and 2) have been synthesized. With one "closed-form" DTE unit, 1 shows aromaticity associated with its conjugated circuit of 26 π-electrons. In contrast, rubyrin 2 containing one "open-form" DTE unit has nonaromatic properties.

View Article and Find Full Text PDF

Structural diversity in expanded porphyrins.

Acc Chem Res

February 2008

Department of Chemistry, Indian Institute of Technology, Kanpur - 208 016, India.

Inspired by the chemistry of porphyrins, in the last decade, a new research area where porphyrin analogues such as expanded, isomeric, and contracted porphyrins have been synthesized, and their chemistry has been exploited extensively. Expanded porphyrins are macrocyclic compounds where pyrrole or heterocyclic rings are connected to each other through meso carbon bridges. Depending on the number of pyrrole rings in conjugation or the number of double bonds linking the four pyrrole rings expanded porphyrins containing up to 64 pi electrons are reported in the literature.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!