Octathienyl/phenyl-substituted zinc phthalocyanines J-aggregated through conformational planarization.

Dalton Trans

The Key Lab of Organic Photoelectrons & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing, 100084, PR China.

Published: January 2011

A novel family of thiophene-decorated phthalocyanines (M-TPcs) was efficiently synthesized, during which the key intermediate of these compounds was purified through a chemical approach. In the optimized geometries of M-TPcs, the peripherally linked thiophene rings are tilted from the Pc core, which oppose aggregation considering the mutual steric hindrance. However, Zn-TPc formed J-aggregates in many solvents while Ni-TPc and Cu-TPc did not. Octaphenyl-substituted zinc Pc (Zn-PPc) showed similar J-aggregation behavior as Zn-TPc. This unusual J-aggregation was attributed to the conformational planarization of the corresponding molecules.

Download full-text PDF

Source
http://dx.doi.org/10.1039/c0dt01066aDOI Listing

Publication Analysis

Top Keywords

conformational planarization
8
octathienyl/phenyl-substituted zinc
4
zinc phthalocyanines
4
phthalocyanines j-aggregated
4
j-aggregated conformational
4
planarization novel
4
novel family
4
family thiophene-decorated
4
thiophene-decorated phthalocyanines
4
phthalocyanines m-tpcs
4

Similar Publications

The incorporation of photoactive organic dyes into layered inorganic materials enhances their optical and chemical properties, making them ideal for sensing applications. In this study, Bisindolyl methane (BIM)-based neutral probes were integrated with bentonite clay to explore their sensing capabilities. Probe 1 (unoxidized BIM) and Probe 2 (oxidized BIM) generally exhibited quenched luminescence in solution due to intramolecular rotations.

View Article and Find Full Text PDF

Benzothiadiazole (BT) has shown promising applications in fullerene solar cells. However, few BT-based polymer donors exhibited a noticeable power conversion efficiency (PCE) for the fused-ring small molecular acceptor-based polymer solar cells (PSCs). Herein, we developed a D-A (D: donor, A: acceptor) polymer donor F-1 based on fluorinated BT (ffBT) as A unit and chlorinated benzo [1,2-b:4,5-b'] dithiophene (BDT-2Cl) as D unit.

View Article and Find Full Text PDF

Achieving Ultrabright NIR-II Nanofluorophore for In Vivo Imaging by Inhibiting H-Aggregates Formation.

Chemistry

December 2024

State Key Laboratory of Pathogenesis, Prevention and Treatment of High Incidence Diseases in Central Asia/School of Medical Engineering and Technology, Xinjiang Medical University, Urumqi, 830054, China.

Small molecules with an acceptor-donor-acceptor (A-D-A) structure, featuring a fused-ring core as the donor and two electron-withdrawing end groups as acceptor units, represent a potential option for NIR-II fluorophores, benefiting from their narrow bandgaps, superior light-harvesting capabilities, and exceptional photostabilities. However, their planar conformations predispose them to forming H-aggregates during self-assembly, leading to significantly reduced fluorescence quantum yield (QY) of the resulting nanofluorophores. Herein, we report a small molecule, PF8CN, with a terminal unit-A-D-A-terminal unit structure.

View Article and Find Full Text PDF

The title compound, CHClNO, is significantly distorted from planarity, with a twist angle between the planes through the hy-droxy-benzene and acetamide groups being 23.5 (2)°. This conformation is supported by intra-molecular C-H⋯O and N-H⋯Cl contacts.

View Article and Find Full Text PDF

Manipulating Backbone Planarity of Ester Functionalized Conjugated Polymer Constitutional Isomer Derivatives Blended with Molecular Acceptors for Controlling Photovoltaic Properties.

Chem Mater

December 2024

School of Chemistry and Biochemistry, School of Materials Science and Engineering, Center for Organic Photonics and Electronics, Georgia Tech Polymer Network, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.

Exploring both electron donor and acceptor phase components in bulk heterojunction structures has contributed to the advancement of organic photovoltaics (OPV) realizing power conversion efficiencies reaching 20%. Being able to control backbone planarity of the donor polymer, while understanding its effects on the polymer conformation and photophysical properties, fosters the groundwork for further achievements in this realm. In this report, three isomeric PM7 derivatives are designed and synthesized where the benzodithiophene-4,8-dione structure is replaced by a quaterthiophene bridge carrying two ester moieties.

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!