Additive- and column-free synthesis of rigid bis-coumarins as fluorescent dyes for G-quadruplex sensing <i>via</i> disaggregation-induced emission

He, Hui-Zi; Li, Kun; Lu, Pinyan; Feng, Mei-Lin; Chen, Shanyong; Yu, Xiao‐Qi

doi:10.1039/d0cc01437k

Cited by 18 publications

(4 citation statements)

References 42 publications

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“…[31][32][33] Surprisingly, there are only a few reports of helicene derivatives comprising of coumarin moiety in extended π-conjugation and their highly fused conjugated geometry could extend the πsystem to enhance both photophysical and optoelectronic properties. [34][35][36][37][38] Coumarin with extended π-conjugation via ortho fused heterocyclic ring can be easily synthesized by the Povarov reaction. Povarov reaction is three component reaction in which aromatic amines initially form aldimines with aldehydes and then undergo [4 + 2] cycloaddition reaction with a variety of substrates including alkyne, alkene, cyclic alkene, enol (ketone, cyclic ketone).…”

Section: Introductionmentioning

confidence: 99%

“…Heterocyclic fused and π‐extended coumarin compounds have been widely used in optical materials, fluorescent dyes, laser dyes, OLEDs, organic solar cells, etc [31–33] . Surprisingly, there are only a few reports of helicene derivatives comprising of coumarin moiety in extended π‐conjugation and their highly fused conjugated geometry could extend the π‐system to enhance both photophysical and optoelectronic properties [34–38] …”

Section: Introductionmentioning

confidence: 99%

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Metal Free Synthesis of Coumarin Containing Hetero[n]helicene like Molecules with TICT and AIE Properties

Soni

Soman

2022

Asian J Org Chem

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Coumarin containing hetero [n]helicene like molecules were synthesized using three component Povarov reaction followed by two dehydrogenation steps in good yields. Synthesis and photophysical properties of coumarin containing multifunctional helicene like molecules were found to be affected by substitution on pendant phenyl ring. Coumarin containing hetero[6]helicene like derivative 10 f showed bright yellow emission in solution, thin film, and solid state. Coumarin containing hetero[6]helicene like compound 13 e showed bright blue emission in solution, thin film, and solid state. The structures of intermediate compounds were confirmed by a single crystal X-ray analysis. These structures were compared with DFT optimized structures for the helicity parameters. DFT calculations provided good correlation with observed photophysical properties of compounds 10 f and 13 e.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Metal Free Synthesis of Coumarin Containing Hetero[n]helicene like Molecules with TICT and AIE Properties

Soni

Soman

2022

Asian J Org Chem

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“…For example, C-MYC transcription was specifically downregulated by the stabilization of G4 in the C-MYC region, which further inhibited the development of triple-negative breast cancer [ 17 ]. The regulation of G4 has been expected as a new anticancer strategy, and many artificial ligands and natural products that interact with G4s are applied in the visualization of G4s and the inhibition of oncogenes [ 18 , 19 ]. Moreover, the stability of G4 was found to be greatly dependent on the surrounding environment.…”

Section: Introductionmentioning

confidence: 99%

Ginsenoside Compound K Assisted G-Quadruplex Folding and Regulated G-Quadruplex-Containing Transcription

et al. 2021

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Ginsenoside compound K (CK) is one of the major metabolites of the bioactive ingredients in Panax ginseng, which presents excellent bioactivity and regulates the expression of important proteins. In this work, the effects of CK on G-quadruplexes (G4s) were quantitatively analyzed in the presence and absence of their complementary sequences. CK was demonstrated to facilitate the formation of G4s, and increase the quantity of G4s in the competition with duplex. Thermodynamic experiments suggested that the electrostatic interactions were important for G4 stabilization by CK. CK was further found to regulate the transcription of G4-containing templates, reduce full-length transcripts, and decrease the transcription efficiency. Our results provide new evidence for the pharmacological study of ginsenosides at the gene level.

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“…In recent years, our group has developed a series of fluorescent probes based on coumarin, , and all the probes show excellent fluorescent properties due to the high fluorescence quantum yield and stable photophysical property of the coumarin skeleton. In addition, the coumarin structure contains a π–π conjugated system that can act on various active sites in organisms through non-covalent interaction methods, such as van der Waals force, π–π electron interaction, hydrogen bonding, hydrophobic interaction, metal coordination, etc., which can improve the mechanical properties and self-healing ability of materials. − At the same time, with good photo-response efficiency and special ring structures, coumarin subsets also play an important part in photo-responsive smart materials. − …”

Section: Introductionmentioning

confidence: 99%

Plant-Inspired Multifunctional Fluorescent Hydrogel: A Highly Stretchable and Recoverable Self-Healing Platform with Water-Controlled Adhesiveness for Highly Effective Antibacterial Application and Data Encryption–Decryption

Wang

et al. 2020

ACS Appl. Mater. Interfaces

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In recent years, hydrogels as an attractive class of intelligent soft materials have been applied in various advanced fields, including electronic materials, wearable devices, and wound dressing materials. However, it still remains a critical challenge to integrate information encryption transmission capability, antibacterial activity, high mechanical performance, adhesiveness, and self-healable ability into one material and achieve the synergistic characteristics through a simple method. In our study, a facile strategy of a plant-inspired hydrogel was proposed, which provides a novel initiator-free photo-cross-linked hydrogel system by simply mixing the coumarin derivative Pho-CA and the monomer in water, and then obtaining the hydrogel Gel-C-Am under the irradiation of UV light without adding any other cross-linking agents and initiators, and this process is very similar to the growth process of plants in nature. This novel hydrogel presents desirable mechanical properties (including twist, stretchability, and recoverability), which exhibits elongation of approximately 1600%. More interestingly, Gel-C-Am hydrogel displays reversible adhesiveness to various substrates (such as glass, paper, leaves, and rubber), and its adhesion properties can be regulated by water: the viscosity disappears when its surface becomes wet, and the viscosity will recover after the water evaporates. In addition, the developed hydrogel has certain self-healable ability. Two pieces of the Gel-C-Am hydrogel can combine together and reshape into one piece in water, and the fused hydrogel has uniform and interconnected pores under SEM. Based on the characteristic of Pho-CA whose fluorescence get recovery after UV irradiation, the hydrogel can be used in the field of encryption and decryption. Also, the resulting Gel-C-Am hydrogel shows an effective antibacterial activity and can potentially be addressed as antibacterial coatings. Taken together, the formation of the novel fluorescent hydrogel system is just like the growth of a plant in the presence of water and light, Pho-CA and the monomer will form a highly stretchable and recoverable self-healing hydrogel with water-controlled adhesiveness. The developed Gel-C-Am hydrogel shows favorable attributes and is suitable for applications in antibacterial polymeric coatings and information encryption transmission.

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Additive- and column-free synthesis of rigid bis-coumarins as fluorescent dyes for G-quadruplex sensing via disaggregation-induced emission

Abstract: A novel and efficient method to synthesize rigid bis-coumarins based on the dimerization of coumarinyl aldehydes was developed.

Cited by 18 publications

References 42 publications

Metal Free Synthesis of Coumarin Containing Hetero[n]helicene like Molecules with TICT and AIE Properties

Metal Free Synthesis of Coumarin Containing Hetero[n]helicene like Molecules with TICT and AIE Properties

Ginsenoside Compound K Assisted G-Quadruplex Folding and Regulated G-Quadruplex-Containing Transcription

Plant-Inspired Multifunctional Fluorescent Hydrogel: A Highly Stretchable and Recoverable Self-Healing Platform with Water-Controlled Adhesiveness for Highly Effective Antibacterial Application and Data Encryption–Decryption

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