A novel fluorophore based on the coupling of AIE and ESIPT mechanisms and its application in biothiol imaging

Chen, Qing; Jia, Chunman; Zhang, Yinfeng; Du, Wei; Wang, Yile; Huang, Yan; Yang, Qian; Zhang, Qi

doi:10.1039/c7tb02076g

Cited by 87 publications

(48 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…AIEE emitters have attracted attention and ESIPT‐active chromophores have been reported to be associated with AIEE characters in many cases . Thus, the molecularly dispersed ESIPT molecular systems often lead to the dramatic reduction of overall light‐emission outputs.…”

Section: Resultsmentioning

confidence: 99%

“…The ESIPT process requires structural relaxations upon proton transfer, and thus a certain conformational freedom is allowed for the molecular structures . The conformational freedom results in allowing the possible nonradiative pathways especially in solution (Figure b), giving AIEE characters to the ESIPT molecules . The AIEE character is advantageous because light outputs from the systems are extremely high embedded into actual devices to avoid the concentration quenching .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Highly Fluorescent Liquid Crystals from Excited‐State Intramolecular Proton Transfer Molecules

Zhang

Sakurai

Aotani

et al. 2018

Advanced Optical Materials

View full text Add to dashboard Cite

solid-state emitters, electroluminescent devices, organic lasers, and so on. [1][2][3][4][5] Particularly, emission through excitedstate intramolecular proton transfer (ESIPT) mechanism with an extremely large Stokes shift [6][7][8][9] (anti-Kasha rule) suppresses excitation energy dissipation via self-absorption, providing attractive material platforms for optical device fabrication. [10,11] ESIPT is a photochemical process that produces a tautomer with a different electronic structure from the original excited form (Figure 1a). The requisite of chemical structures for ESIPT is the presence of an intramolecular hydrogen bond (H-bond) between the proton donor (OH and NH 2 ) and the proton acceptor (N and CO) groups close to one another in a single molecule. Recent notable reports on the ESIPT fluorophores include the polymorph-dependent emissive crystals, [12,13] double proton transfer process with an extra-large Stokes shift, [14] amplified spontaneous emission, [15][16][17] lasing system, [18][19][20] environment-sensitive multicolored materials, [21][22][23][24] and the use as emitters with electrically generated intramolecular proton transfers. [25] Most of ESIPT molecules show significant fluorescence in the solid states, not suffering from "concentration quenching" and thus serving as aggregation-induced emission enhancement (AIEE) materials. [26][27][28] The ESIPT process requires structural relaxations upon proton transfer, and thus a certain conformational freedom is allowed for the molecular structures. [29] The conformational freedom results in allowing the possible nonradiative pathways especially in solution (Figure 1b), giving AIEE characters to the ESIPT molecules. [30,31] The AIEE character is advantageous because light outputs from the systems are extremely high embedded into actual devices to avoid the concentration quenching. [32] However, most of the previous ESIPT as well as AIEE systems have been mostly reported in the rigid solid phase such as single crystals, polycrystals, or powders [11,12] -not in liquid crystals (LCs). Although columnar LCs with ESIPT-active cores were reported, [33,34] simple rod-shaped LC molecules embedded with ESIPT-active group have been limited. [35,36] In contrast to columnar and cubic liquid crystal phases with highly ordered structures, nematic as well as several smectic subphases can easily align macroscopically by rubbed surfaces, mechanical stimuli, and electric and magnetic fields. [37][38][39] Fluorescence via excited-state intramolecular proton transfer (ESIPT) provides strong light emission with a large Stokes shift and environment-sensitive unique spectral patterns. Particular systems including 2-(2-hydroxyphenyl) benzothiazole (HBT) serve as efficient solid-state emitters with the ESIPT mechanism and aggregation-induced emission enhancement (AIEE) property, but have not been used for liquid crystalline (LC) materials. Here, rod-shaped fluorescent LCs with ESIPT characters are newly developed based on the HBT motif. The design of the targeted mole...

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Highly Fluorescent Liquid Crystals from Excited‐State Intramolecular Proton Transfer Molecules

Zhang

Sakurai

Aotani

et al. 2018

Advanced Optical Materials

View full text Add to dashboard Cite

show abstract

“…In fact, probe 84 displayed high sensitivity (LOD = 72 nM) and excellent selectivity over other biologically relevant analytes. 214 Lin and co-workers reported an aggregate based AIE + ESIPT fluorescent probe 85 for SO 2 /SO 3…”

Section: Fluorescence Based Sensors With a Combined Fluorescence Mechmentioning

confidence: 99%

Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Recently, the development of aggregation‐induced emission‐ESIPT dual‐mechanism‐based fluorophores has attracted increasing interest recently. Specially, a novel fluorophore tetraphenylethene‐2‐(2′‐hydroxyphenyl)benzothiazole (TPE‐HBT) was designed and synthesized based on the intersection of TPE and HBT by Chen et al Tetraphenylethene‐2‐(2′‐hydroxyphenyl)benzothiazole could be converted into a novel biothiols responding probe, which is suitable for biothiol imaging in living cell systems . The HBT part has exclusively intramolecular O–H … N hydrogen bonds, which form a rather strong quasi‐aromatic chelating ring, possessing the potential possibility for proton transfer.…”

Section: Introductionmentioning

confidence: 99%

Theoretical investigation on the excited state intramolecular proton coupled charge transfer phenomenon for a novel fluorophore

Yin

Shi

2018

J of Physical Organic Chem

View full text Add to dashboard Cite

We theoretically investigate the excited state behaviors of the novel fluorophore tetraphenylethene-2-(2′-hydroxyphenyl)benzothiazole (TPE-HBT), which was designed based on the intersection of TPE and HBT, using density functional theory and time-dependent density functional theory methods. Compared with previous experimental results about fluorescence peaks, our calculated results are in good agreement with experimental data, which further confirms that the theoretical level we used is reasonable. Furthermore, our results confirm that the excited state intramolecular proton transfer (ESIPT) process happens upon photoexcitation, which is distinctly monitored by the infrared spectra and the potential energy curves. In addition, the calculation of highest occupied molecular orbital and lowest unoccupied molecular orbital reveals that the electron density change of proton acceptor because of the intramolecular charge transfer (ICT) process in the S 1 state induces the ESIPT. Moreover, the transition density matrix is worked out to facilitate deeper insight into the ESIPT coupled ICT process. It is hoped that the present work not only elaborates the ESIPT coupled ICT phenomenon and corresponding mechanisms for the TPE-HBT but also may be helpful to design and develop new materials and applications involved in TPE-HBT systems in future.KEYWORDS excited state intramolecular proton transfer, intramolecular charge transfer, potential energy curves, time-dependent density functional theory

show abstract

A novel fluorophore based on the coupling of AIE and ESIPT mechanisms and its application in biothiol imaging

Abstract: A novel fluorophore TPE-HBT was designed based on the intersection of tetraphenylethene (TPE) and 2-(2′-hydroxyphenyl)benzothiazole (HBT).

Cited by 87 publications

References 37 publications

Highly Fluorescent Liquid Crystals from Excited‐State Intramolecular Proton Transfer Molecules

Highly Fluorescent Liquid Crystals from Excited‐State Intramolecular Proton Transfer Molecules

Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents

Theoretical investigation on the excited state intramolecular proton coupled charge transfer phenomenon for a novel fluorophore

Contact Info

Product

Resources

About