2,5-bis(4-alkoxycarbonylphenyl)-1,4-diaryl-1,4-dihydropyrrolo[3,2-b ]pyrrole (AAPP ) AIEgens: tunable RIR and TICT characteristics and their multifunctional applications

Chemical Science
Kai LiBen Zhong Tang

Abstract

Aggregation-induced emission luminogens (AIEgens) have attracted extensive interest for their outstanding luminescence properties in the aggregated state and even in the solid state. In this work, we developed a series of novel AIEgens based on 2,5-bis(4-alkoxycarbonylphenyl)-1,4-diaryl-1,4-dihydropyrrolo[3,2-b]pyrrole (AAPP). The AIEgens can be facilely synthesized through a single-step reaction under mild conditions with satisfactory yields. Interestingly, AAPP was found to have multiple luminous mechanisms that result in variable fluorescence properties. The propeller-like structure of AAPP enables a restricted intramolecular rotation (RIR) process which significantly enhances its fluorescence in the aggregated state (i.e. AIE fluorescence). In addition, there is a donor-acceptor interaction between the heterocycle center and the alkoxycarbonyl units in AAPP which allows a typical twisted intramolecular charge transfer (TICT) process in the dispersed state, resulting in strong fluorescence emissions in non-polar or low-polarity solvents but fluorescence quenching in high-polarity solvents. Due to the tunable RIR and TICT processes and the multiple fluorescence, AAPP compounds exhibit multifunctional applications: (1) as a re...Continue Reading

References

Dec 31, 2002·Toxicology Letters·Soisungwan SatarugMichael R Moore
Feb 4, 2005·Biometals : an International Journal on the Role of Metal Ions in Biology, Biochemistry, and Medicine·Robert A GoyerMichael P Waalkes
Nov 14, 2008·Journal of the American Chemical Society·Tanyu ChengLiping Duan
Jan 31, 2009·The Journal of Organic Chemistry·Weixin TangAijun Tong
Jul 15, 2009·Chemical Communications : Chem Comm·Yuning HongBen Zhong Tang
Apr 29, 2010·Physical Chemistry Chemical Physics : PCCP·Akitaka ItoNoboru Kitamura
Jul 30, 2011·Chemical Society Reviews·Yuning HongBen Zhong Tang
Dec 21, 2011·Chemical Society Reviews·Ha Na KimJuyoung Yoon
Jun 8, 2013·Accounts of Chemical Research·Dan DingBen Zhong Tang
Mar 25, 2014·The Journal of Organic Chemistry·Maciej KrzeszewskiDaniel T Gryko
Apr 16, 2014·Chemical Society Reviews·Rongrong HuBen Zhong Tang
Jul 1, 2014·Advanced Materials·Ju MeiBen Zhong Tang
Nov 7, 2014·Chemical Society Reviews·Ryan T K KwokBen Zhong Tang
Feb 13, 2015·Chemical Communications : Chem Comm·Lifang ZhangYong Wang
Jan 23, 2016·Chemical Communications : Chem Comm·Qi FengHongwei Hou
Mar 28, 2017·Journal of the American Chemical Society·Hiroyuki TsujimotoTimothy M Swager
Oct 1, 2015·Chemical Science·Zujin ZhaoBen Zhong Tang
Mar 1, 2015·Chemical Science·Ming ChenBen Zhong Tang

❮ Previous
Next ❯

Citations

Jul 13, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Chris S HawesThorfinnur Gunnlaugsson
Jul 18, 2018·Chemistry : a European Journal·Yunxiang LeiYuping Dong
Jan 23, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Yuan TianThomas C W Mak
Apr 18, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Di WuFrançois Mathey
Aug 3, 2019·Chemistry : a European Journal·Brunella BardiFrancesca Terenziani
Apr 8, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Yaqi YangBen Zhong Tang
Sep 3, 2020·Chemical Science·Zhiyun ZhangHe Tian
Jun 21, 2018·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Lu PengAijun Tong
Mar 25, 2020·Chemical Science·Hua-Qing YinXue-Bo Yin
Dec 12, 2018·Chemistry : a European Journal·Zhong WeiShuang-Quan Zang
Nov 12, 2019·Organic Letters·Keita TajimaHiroshi Shinokubo
Feb 16, 2021·Journal of Drug Targeting·Rashmi Kumari, Dhanya Sunil
Jul 25, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rosita Diana, Barbara Panunzi
Sep 11, 2020·The Journal of Organic Chemistry·Mariusz TasiorDaniel T Gryko
May 22, 2018·Journal of the American Chemical Society·Jian-Hong TangPeter J Stang
May 22, 2020·ACS Applied Materials & Interfaces·Lingchen MengWenjing Tian
Dec 29, 2021·The Journal of Physical Chemistry Letters·You LiDajun Ding

❮ Previous
Next ❯

Methods Mentioned

BETA
Fluorescence
light scattering
dynamic light scattering
X-ray

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.