Stimulus-responsive water soluble synthetic nanographene

Ma, Shuang; Zhu, Yanpeng; Dou, Wei‐Tao; Chen, Ying; He, Xiao‐Peng; Wang, Jiaobing

doi:10.1007/s11426-020-9916-7

“…NIR fluorescent probes are highly desirable and valuable for bio-imaging because NIR light (650–900 nm) has advantages that include low photodamage to biological samples, superior tissue penetration, and low background auto-fluorescence from biomolecules present in living systems. − Some water-soluble nanographene molecules have been successfully used in bio-imaging applications. − Considering the high dispersibility of N-Q7H in polar solvents, such as dimethyl sulfoxide (Figure S18), and its high NIR fluorescence quantum yield, we evaluated the potential of N-Q7H for imaging HeLa cells. The HeLa cells were incubated with a 10 μg/mL dimethyl sulfoxide solution of N-Q7H for 24 h at 37 °C (Figure a) and then stained with the Hoechst 33342 DNA-specific nuclear fluorescent probe (Figure b).…”

Section: Resultsmentioning

confidence: 99%

Nitrogen-Embedded Quintuple [7]Helicene: A Helicene–Azacorannulene Hybrid with Strong Near-Infrared Fluorescence

Wu

¹

,

Ying

²

,

Su

³

et al. 2022

View full text Add to dashboard Cite

Herein, a nitrogen-embedded quintuple [7]helicene (N-Q7H) with an azapentabenzocorannulene core, which can be considered to be a helicene/azacorannulene hybrid π-system, was synthesized from azapentabenzocorannulene in a three-step process. N-Q7H is the first example of a multiple helicene with an azabuckybowl core. Single-crystal X-ray diffractometry unambiguously confirmed the structure of the propeller-shaped hybrid π-system. Owing to nitrogen-atom doping in the multiple helicenes and effective hybridization between the helicene and azacorannulene, N-Q7H exhibits considerably redshifted absorption and emission (yellow-to-green color change and green-to-near-infrared fluorescence change) relative to the azapentabenzocorannulene core. The broad absorption from the ultraviolet–visible to the NIR region is ascribable to the allowed transition between the highest occupied molecular orbital and the lowest unoccupied molecular orbital after symmetry breaking, as revealed by density functional theory calculations. Compared to previous propeller-shaped multiple helicenes with corannulene or hexabenzocoronene (etc.) as cores, N-Q7H demonstrates a significantly higher NIR fluorescence quantum efficiency of 28%. Additionally, the chiral-resolution and redox properties of N-Q7H were investigated. The excellent photophysical and inherent chiral properties of N-Q7H suggest that azapentabenzocorannulene can be used as an outstanding nitrogen-embedded core to construct novel multiple helicenes with wide application potential, including as NIR fluorescent bio-probes.

show abstract

“…In order to further extend possible applications, for example in biological or medicinal research, the development of highly‐soluble/hydrophilic molecules is desirable [8, 9] . The most conventional method to achieve water‐soluble polycyclic aromatic molecules is to add hydrophilic substituents at their peripheral positions (Figure 1a) [10–16] . However, the method may not be ideal in terms of step economy as it requires some additional steps for functionalization.…”

Section: Figurementioning

confidence: 99%

Diazapentabenzocorannulenium: A Hydrophilic/Biophilic Cationic Buckybowl

Li

¹

,

Hamamoto

²

,

Kwek

³

et al. 2021

View full text Add to dashboard Cite

Polycyclic aromatic molecules are promising functional materials for a wide range of applications, especially in organic electronics. However, their largely hydrophobic nature has impeded further applications. As such, imparting high solubility/hydrophilicity to polycyclic aromatic molecules leads to a breakthrough in this research field. Herein, we report the synthesis of diazapentabenzocorannulenium, a cationic nitrogen-embedded buckybowl bearing a central imidazolium core, by a bottom-up strategy from polycyclic aromatic azomethine ylide. X-ray crystallography analyses have revealed a bowl-shaped molecular structure that is capable of forming charge-segregated one-dimensional columns by bowl-in-bowl packing. In addition to its fluorescence capabilities and high dispersibility in water, the molecule was found to selectively localize in the mitochondria of various tumor cells, showing potential as viable mitochondriaselective fluorescent probes.Polycyclic aromatic molecules are one of the most important class of organic molecules owing to their widespread applications in various scientific fields. [1][2][3][4][5] The significant progress and application of polycyclic aromatic molecules in material sciences, especially in organic electronics, are mainly based on their intrinsic hydrophobic properties. [6,7] In order to further extend possible applications, for example in biological or medicinal research, the development of highlysoluble/hydrophilic molecules is desirable. [8,9] The most conventional method to achieve water-soluble polycyclic aromatic molecules is to add hydrophilic substituents at their peripheral positions (Figure 1a). [10][11][12][13][14][15][16] However, the method may not be ideal in terms of step economy as it requires some additional steps for functionalization. It is therefore essential to develop more efficient methods in introducing hydrophilicity to polycyclic aromatic molecules by other methods than introducing hydrophilic substituents. A possible solution would be to change the framework of polycyclic aromatic molecules. Firstly, the introduction of curvature to Angewandte Chemie

show abstract

“…In order to further extend possible applications, for example in biological or medicinal research, the development of highly‐soluble/hydrophilic molecules is desirable [8, 9] . The most conventional method to achieve water‐soluble polycyclic aromatic molecules is to add hydrophilic substituents at their peripheral positions (Figure 1a) [10–16] . However, the method may not be ideal in terms of step economy as it requires some additional steps for functionalization.…”

Section: Figurementioning

confidence: 99%

Diazapentabenzocorannulenium: A Hydrophilic/Biophilic Cationic Buckybowl

Li

¹

,

Hamamoto

²

,

Kwek

³

et al. 2021

View full text Add to dashboard Cite

Polycyclic aromatic molecules are promising functional materials for a wide range of applications, especially in organic electronics. However, their largely hydrophobic nature has impeded further applications. As such, imparting high solubility/hydrophilicity to polycyclic aromatic molecules leads to a breakthrough in this research field. Herein, we report the synthesis of diazapentabenzocorannulenium, a cationic nitrogen‐embedded buckybowl bearing a central imidazolium core, by a bottom‐up strategy from polycyclic aromatic azomethine ylide. X‐ray crystallography analyses have revealed a bowl‐shaped molecular structure that is capable of forming charge‐segregated one‐dimensional columns by bowl‐in‐bowl packing. In addition to its fluorescence capabilities and high dispersibility in water, the molecule was found to selectively localize in the mitochondria of various tumor cells, showing potential as viable mitochondria‐selective fluorescent probes.

show abstract

Stimulus-responsive water soluble synthetic nanographene

Cited by 9 publications

References 37 publications

Nitrogen-Embedded Quintuple [7]Helicene: A Helicene–Azacorannulene Hybrid with Strong Near-Infrared Fluorescence

Nitrogen-Embedded Quintuple [7]Helicene: A Helicene–Azacorannulene Hybrid with Strong Near-Infrared Fluorescence

Diazapentabenzocorannulenium: A Hydrophilic/Biophilic Cationic Buckybowl

Diazapentabenzocorannulenium: A Hydrophilic/Biophilic Cationic Buckybowl

Contact Info

Product

Resources

About