Strong solvent dependence of linear and non-linear optical properties of donor–acceptor type pyrrolo[3,2-b]pyrroles

Literature Information

Publication Date 2015-07-08
DOI 10.1039/C5CP03523F
Impact Factor 3.676
Authors

Rafał Orłowski, Marzena Banasiewicz, Guillaume Clermont, Frédéric Castet, Rashid Nazir, Mireille Blanchard-Desce, Daniel T. Gryko


View Original

Abstract

We describe the design, synthesis, and fluorescent profile of two environment-sensitive dyes in which an electron-donating group is conjugated to an electron-accepting unit via a pyrrolo[3,2-b]pyrrole ring system. The maximum emission wavelength (λem) of these donor–donor–acceptor (D–D–A) pyrrolo[3,2-b]pyrroles was found to be very sensitive to the environment (a bathochromic shift of about 100 nm in polar solvents). The longer emission wavelength in polar aprotic as well as hydrophilic solvents compared with that in low-polarity hydrophobic solvents was due to an ICT character of the excited state. The Stokes shift increased in both cases following the polarity differences, reaching ∼7000 cm−1 in MeOH for the compound possessing a cyano group and dimethylamino groups at the periphery. Interestingly, the two-photon absorption responses were also found to be quite sensitive to solvent polarity with an increase by a factor of about 2 on going from an apolar solvent to a highly polar protic or aprotic solvent.

Related Literature

A procedure for the preparation of Ti-Beta zeolites for catalytic epoxidation with hydrogen peroxide

Bo Tang, Weili Dai, Naijia Guan, Landong Li, Michael Hunger

2014-01-20 Paper

DOI: 10.1039/C3GC42534G

The potential of methylsiloxanes as solvents for synthetic chemistry applications

Mohd Azri Ab Rani, Nadine Borduas, Victoria Colquhoun, Robert Hanley, Henry Johnson, Solène Larger, Paul D. Lickiss, Veronica Llopis-Mestre, Selina Luu, Martin Mogstad, Philipp Oczipka, James R. Sherwood, Tom Welton, Jun-Yi Xing

2013-11-21 Paper

DOI: 10.1039/C3GC42036A

Catalyst-free transformation of levulinic acid into pyrrolidinones with formic acid

Yawen Wei, Chao Wang, Xue Jiang, Dong Xue, Zhao-Tie Liu

2013-11-11 Communication

DOI: 10.1039/C3GC42125B

Asymmetric hydrogenation of unprotected indoles using iridium complexes derived from P–OP ligands and (reusable) Brønsted acids

José Luis Núñez-Rico, Héctor Fernández-Pérez

2013-12-19 Communication

DOI: 10.1039/C3GC42132E

Ruthenium on chitosan: a recyclable heterogeneous catalyst for aqueous hydration of nitriles to amides

R. B. Nasir Baig, Mallikarjuna N. Nadagouda, Rajender S. Varma

2013-12-19 Communication

DOI: 10.1039/C3GC42004C

Glycerol: a solvent and a building block of choice for microwave and ultrasound irradiation procedures

P. Cintas, S. Tagliapietra, E. Calcio Gaudino, G. Palmisano, G. Cravotto

2013-12-09 Critical Review

DOI: 10.1039/C3GC41955J

Heterogeneous catalytic reaction of microcrystalline cellulose in hydrothermal microwave-assisted decomposition: effect of modified zeolite Beta

José González-Rivera, Ignacio R. Galindo-Esquivel, Massimo Onor, Emilia Bramanti, Iginio Longo, Carlo Ferrari

2013-11-27 Paper

DOI: 10.1039/C3GC42207K

Electrocarboxylation of acetophenone in ionic liquids: the influence of proton availability on product distribution

Mike Horne, Alan M. Bond, Jie Zhang

2014-01-06 Paper

DOI: 10.1039/C3GC42404A

A carbon-based photocatalyst efficiently converts CO2 to CH4 and C2H2 under visible light

Tongshun Wu, Luyi Zou, Dongxue Han, Fenghua Li, Qixian Zhang, Li Niu

2014-01-08 Communication

DOI: 10.1039/C3GC42454E

Glycerol based solvents: synthesis, properties and applications

José I. García, Héctor García-Marín, Elísabet Pires

2013-12-05 Critical Review

DOI: 10.1039/C3GC41857J

You might also like

Compound Q&A

What precautions should be taken when handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3)?

When handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3), safety go...

40716-16-34-Methyl-6-(trifluor...
Compound Q&A

What is 4-(3,5-Difluorophenyl)aniline (CAS: 405058-00-6)?

4-(3,5-Difluorophenyl)aniline is an aromatic organic compound with the CAS numbe...

405058-00-64-(3,5-Difluoropheny...
Compound Q&A

How is 5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid (CAS: 338982-07-3) typically synthesized?

5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid can ...

338982-07-35-{[4-(Trifluorometh...
Compound Q&A

What is the market or research trend for 4-Benzylaniline hydrochloride (CAS: 6317-57-3)?

The market for 4-Benzylaniline hydrochloride (CAS: 6317-57-3) is steadily growin...

6317-57-34-Benzylaniline hydr...
Compound Q&A

Is [3-(Diethylsulfamoyl)phenyl]boronic acid (CAS: 871329-58-7) safe?

[3-(Diethylsulfamoyl)phenyl]boronic acid is generally considered safe when handl...

871329-58-7[3-(Diethylsulfamoyl...
Compound Q&A

What are the main uses of 3-Bromo-2,5-dimethoxyaniline (CAS: 115929-62-9)?

3-Bromo-2,5-dimethoxyaniline is mainly used in the pharmaceutical and chemical i...

115929-62-93-Bromo-2,5-dimethox...
Compound Q&A

What regulatory guidelines apply to N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7)?

N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7) is subject to ...

915922-67-7N-Methyl-1-(5-methyl...
Compound Q&A

What industries use Carbamic acid, N-[(5S)-5,6-diamino-6-oxohexyl]-, 1,1-dimethylethyl ester (CAS: 24828-96-4)?

This compound is primarily used in the pharmaceutical industry for the synthesis...

24828-96-4Carbamic acid, N-[(5...
Compound Q&A

How should 2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) be stored?

2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) sho...

1298101-47-92-Methyl-2-propanyl ...
Compound Q&A

What industries use Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9)?

Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9) is utilized in the pharma...

367-33-9Ethyl 2-bromo-4,4,4-...

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.