Rational design of asymmetric red fluorescent probes for live cell imaging with high AIE effects and large two-photon absorption cross sections using tunable terminal groups

Chang, Zhengfeng; Jing, Ling-Min; Chen, Bin; Zhang, Mengshi; Cai, Xiaolei; Liu, Junjie; Ye, Yanchun; Lou, Xiaoding; Zhao, Zujin; Liu, Bin; Wang, Jinliang; Tang, Ben Zhong

doi:10.1039/c5sc04920b

Cited by 99 publications

(23 citation statements)

References 70 publications

(19 reference statements)

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“…Since the intriguing discovery of the aggregation-induced emission (AIE) by Tang et al [11], it has received intense research interest as it is opposite to aggregation-caused quenching mechanism. Luminogens with AIE characteristics can fluoresce strongly in the aggregate state, which opens a new avenue towards efficient solid-state light emitters [12,13], bioprobes [14][15][16][17][18], and chemosensors [19][20][21][22]. However, the current AIE systems are mainly focused on silole, tetraphenylethene (TPE) and cyanostilbene derivatives, which show short-wavelength fluorescence in the range of 400-600 nm.…”

Section: Introductionmentioning

confidence: 99%

Galactose functionalized diketopyrrolopyrrole as NIR fluorescent probes for lectin detection and HepG2 cell targeting based on aggregation-induced emission mechanism

et al. 2018

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Since the elucidation that sugar-lectin interactions contribute to the understanding of ''Glycomics'', how to construct glycosensors with rapid response, excellent sensitivity and selectivity is of intense research interest. Herein, we report the design of three NIR emissive glyco-probes based on diketopyrrolopyrrole (DPPs) conjugated with two (DPPG), four (DPPF-G) and six (DPPS-G) galactose groups. All three molecules could probe lectins with excellent sensitivity and selectivity. The increase of glyco-DPP emission in NIR region upon interaction with lectin is due to the aggregates formation induced by sugar-lectin interactions, which have been verified by dynamic light scattering (DLS) and scanning electronic microscope (SEM) analysis. Due to the multiple glyco-ligands on DPPS-G, it has been successfully used to stain HepG2 cells through interactions between galactose and asialogly-coprotein (ASGP-R), which are overexpressed on the surface of HepG2 cells.

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Section: Introductionmentioning

confidence: 99%

Galactose functionalized diketopyrrolopyrrole as NIR fluorescent probes for lectin detection and HepG2 cell targeting based on aggregation-induced emission mechanism

et al. 2018

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“…With the developments and increased availability of short pulse (picosecond and femtosecond) lasers, the studies of TPA became more widespread and detailed in the 1990s, and much information has been collected on the materials that provide effective Molecules 2021, 26, 6323 2 of 39 TPA. Many applications of this effect, such as those in photodynamic therapy (PDT) [5][6][7], optical data storage [8,9], optical power limiting [10], imaging [11,12], 3D photopolymerization [13,14], microfabrication and lithography [15][16][17], photodiodes [18,19], and laser pulse characterization [20] have been suggested. Applications of TPA exploit several features of this phenomenon.…”

Section: Introduction 1tpa and Its Applicationsmentioning

confidence: 99%

Prospects for More Efficient Multi-Photon Absorption Photosensitizers Exhibiting Both Reactive Oxygen Species Generation and Luminescence

et al. 2021

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The use of two-photon absorption (TPA) for such applications as microscopy, imaging, and photodynamic therapy (PDT) offers several advantages over the usual one-photon excitation. This creates a need for photosensitizers that exhibit both strong two-photon absorption and the highly efficient generation of reactive oxygen species (ROS), as well as, ideally, bright luminescence. This review focuses on different strategies utilized to improve the TPA properties of various multi-photon absorbing species that have the required photophysical properties. Along with well-known families of photosensitizers, including porphyrins, we also describe other promising organic and organometallic structures and more complex systems involving organic and inorganic nanoparticles. We concentrate on the published studies that provide two-photon absorption cross-section values and the singlet oxygen (or other ROS) and luminescence quantum yields, which are crucial for potential use within PDT and diagnostics. We hope that this review will aid in the design and modification of novel TPA photosensitizers, which can help in exploiting the features of nonlinear absorption processes.

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“…As the advent of high power laser, two‐photon absorption (TPA) in the near‐infrared (NIR) window I (650‐950 nm) and II (1000‐1350 nm) has drawn considerable interests in experimental and theoretical fields due to its outstanding applications in in vivo imaging, frequency up‐conversion, three‐dimensional optical data/information storage, photodynamic therapy, optical limiting and so on . Therefore, the design and synthesis of new organic materials with large TPA cross‐sections are increasingly demanded . As a result, various molecular design strategies are proposed .…”

Section: Introductionmentioning

confidence: 99%

Chiral thiophene derivatives with optimal two‐photon absorption in near‐infrared window I and II

Wang

Ren

et al. 2018

Int J of Quantum Chemistry

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Thiophene derivatives are outstanding organic materials due to their wide spectral response, superior optoelectronic properties, and excellent environmental stability, which have attracted widespread attention in both theory and applications. However, their chiral analogues and corresponding chiroptical behaviors have been rarely investigated. Herein, a series of chiral thiophene derivatives are firstly designed by taking both optical chirality and two‐photon absorption (TPA) response into consideration, and are then investigated by modern analytical response theory. The calculated results demonstrate that these novel chiral thiophene derivatives show optimal TPA in the near‐infrared (NIR) window I and II, indicating that they are promising for biological applications. More importantly, they exhibit reasonable two‐photon circular dichroism (TPCD) signals, which are desirable candidates for chiral recognition regions. Furthermore, the calculations of orbital transitions shed light on that the intramolecular charge transfer plays an important role in their excellent TPA and TPCD behaviors in NIR regions.

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Rational design of asymmetric red fluorescent probes for live cell imaging with high AIE effects and large two-photon absorption cross sections using tunable terminal groups

Abstract: Donor–acceptor π-conjugated aggregation-induced red emission materials for live cell imaging.

Cited by 99 publications

References 70 publications

Galactose functionalized diketopyrrolopyrrole as NIR fluorescent probes for lectin detection and HepG2 cell targeting based on aggregation-induced emission mechanism

Galactose functionalized diketopyrrolopyrrole as NIR fluorescent probes for lectin detection and HepG2 cell targeting based on aggregation-induced emission mechanism

Prospects for More Efficient Multi-Photon Absorption Photosensitizers Exhibiting Both Reactive Oxygen Species Generation and Luminescence

Chiral thiophene derivatives with optimal two‐photon absorption in near‐infrared window I and II

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