Synthesis, aggregation-enhanced emission, polymorphism and piezochromism of TPE-cored foldamers with through-space conjugation

Zhuang, Zeyan; Shen, Pingchuan; Ding, Siyang; Luo, Wenwen; He, Bo; Wang, Bohan; Huang, Tianbai; Hu, Rongrong; Qin, Anjun; Zhao, Zujin; Tang, Ben Zhong

doi:10.1039/c6cc04233c

Cited by 33 publications

(18 citation statements)

References 32 publications

(5 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The archetypal foldamer, Z-o-BPTPE, has been confirmed by crystallographic analysis to be a cis-isomer. The specific phenyl rings, Φ 1 and Φ 2 , are stacked in a nearly parallel manner, with a plane overlap of about 50% and inter-ring distances of 3.147 and 3.166 Å (Figure 6), [55][56][57] indicating the existence of efficient electronic coupling between the stacked phenyl rings. Compared with the conventional [2.2]pCp, Z-o-BPTPE performs better in photoluminescence and charge transport.…”

Section: New Through-space Conjugated Systemmentioning

confidence: 99%

“…Moreover, by exploring other TPE-cored foldamers with different branched chains, we have concluded that the substituents with a different electronic nature and heterocycles can regulate the stacking geometry and optical properties, but show no apparent impact on the formation of a folded architecture. These foldamers exhibit an efficient through-space conjugation and aggregationenhanced emission (AEE) [55][56][57][58][60][61][62][63] property because of the increased molecular rigidity. In view of this observation, regulating the geometric and electronic structures of the foldamers to control the degree of through-space conjugation should be helpful for manipulating photophysical properties and potential functions.…”

Section: New Through-space Conjugated Systemmentioning

confidence: 99%

See 1 more Smart Citation

Through-Space Conjugation: A Thriving Alternative for Optoelectronic Materials

Li¹,

Shen²,

Zhao³

et al. 2019

CCS Chem

Self Cite

138

View full text Add to dashboard Cite

Efficient electronic coupling is the key to constructing optoelectronic functional π systems. Generally, the delocalization of π electrons must comply with the framework constructed by covalent bonds (typically σ bonds), representing classic through-bond conjugation. However, through-space conjugation offers an alternative that achieves spatial electron communication with closely stacked π systems instead of covalent bonds thus enabling multidimensional energy and charge transport. Because of the ever-accelerating advances of through-space conjugation studies, researchers are inspired greatly by the beauty of through-space conjugated systems and their potential in high-tech applications. In this mini review, we introduce some representative and newly developed π systems having the through-space conjugation feature. In addition to discussing the profound impacts of through-space conjugation on the luminescence properties and charge transport, we will review some impressive findings of distinctive molecules with attractive characteristics, such as aggregation-induced emission, thermally activated delayed fluorescence, bipolar charge transport, and multichannel. These achievements may bring about new breakthroughs of theory, materials, and devices in the fields of organic electronics and molecular electronics.

show abstract

Section: New Through-space Conjugated Systemmentioning

confidence: 99%

Section: New Through-space Conjugated Systemmentioning

confidence: 99%

Through-Space Conjugation: A Thriving Alternative for Optoelectronic Materials

Li¹,

Shen²,

Zhao³

et al. 2019

CCS Chem

Self Cite

138

View full text Add to dashboard Cite

show abstract

“…Accordingly,avariety of aromatic groups were introduced at the ortho position of benzophenone to construct as eries of (Z)-TPE derivatives. [80][81][82][83][84][85][86] The chemical structures of these compounds are showninFigure 17, along with their corresponding CCDC numbers. [98] The simplest( Z)-o-BPTPE served as the core of the Z derivatives.…”

Section: Stereoselective Synthesis Of Pure (Z)-/(e)-tpe Isomersmentioning

confidence: 99%

Recent Advances in the Z/E Isomers of Tetraphenylethene Derivatives: Stereoselective Synthesis, AIE Mechanism, Photophysical Properties, and Application as Chemical Probes

Xie

2019

Chemistry An Asian Journal

View full text Add to dashboard Cite

Focused research on the Z/E isomerso ft etraphenylethene (TPE) derivatives is scarce in comparison with the thousands of luminogens with AIE properties (AIEgens) that have been synthesized based on the TPE moiety.T he similar chemical and physical properties of the Z/E isomersm ake them difficult to separate by using conventional chromatographic techniques.H owever,t hey can be isolated by introducing polar groupsa nd the pure isomers exhibit very different photophysical properties, mechanochromism, and host-guestc oordination,a sw ell as assisting in deciphering the AIE mechanism. In this Minireview, we present an overview of the disagreement regarding the AIE mechanism between the restriction of intramolecular vibration and photoinduced Z/E isomerization. Then, we discuss the development of (Z)-/(E)-TPE derivatives, their use in host-guest detection, and their mechanoluminescence properties, with a focus on their photophysical characteristics. Finally,w ee xplore the stereoselective synthesis of pure (Z)-/(E)-TPE derivatives.

show abstract

“…In previous work, we established a new class of hybrid conjugation system of tetraphenylethene (TPE)-cored foldamers, which employ TPE as a TBC core and fold a pair of aryl wings (fragments or chains) into a π-stacking TSC component. [46][47][48][49] Utilizing such a fantastic geometry, efficient luminescent materials, bipolar carrier transporting materials, 50 and multichannel single-molecular wires 51,52 have been successfully created. In addition, preliminary investigations on the structure-property correlation have been carried out.…”

Section: Introductionmentioning

confidence: 99%

Deciphering Benzene–Heterocycle Stacking Interaction Impact on the Electronic Structures and Photophysical Properties of Tetraphenylethene-Cored Foldamers

Zhuang

Shen

et al. 2022

CCS Chem

Self Cite

View full text Add to dashboard Cite

Conjugation, as an essential chemical term used to describe electron delocalization, can be roughly grouped into two categories, through-bond conjugation (TBC) and through-space conjugation (TSC). A hybrid conjugation system integrating both TBC and TSC is rarely studied and utilized, for lack of a well-established model and difficulty of structure modification and property tuning, despite its theoretical significance and potential applications. Herein, various foldamers with a tetraphenylethene (TPE) core are employed as hybrid conjugation models to investigate structure-property correlation by introducing heterocycles of furan/thiophene into the π-stacking TSC component. For comparison, two kinds of TPE-cored foldamers with different stacking models, a benzene-heterocycle stacking model and a benzene-benzene stacking model, are designed. Combining experimental measurements and theoretical calculations, the impact of benzene-heterocycle interaction on the hybrid conjugation natures and photophysical properties has been studied systematically. The results reveal that the benzene-heterocycle stacking model can fabricate a hybrid conjugation nature with an improved TSC component to make a more dominant contribution to the electronic transition natures than the benzene-benzene stacking model, leading to the distinguishing photophysical behavior. This work provides valuable guidance for the design of new functional materials with hybrid conjugation systems.

show abstract

Synthesis, aggregation-enhanced emission, polymorphism and piezochromism of TPE-cored foldamers with through-space conjugation

Abstract: A series of new folded tetraphenylethene derivatives with different substituents are stereoselectively synthesized, which exhibit interesting through-space conjugation, aggregation-enhanced emission, polymorphism and piezochromism properties.

Cited by 33 publications

References 32 publications

Through-Space Conjugation: A Thriving Alternative for Optoelectronic Materials

Through-Space Conjugation: A Thriving Alternative for Optoelectronic Materials

Recent Advances in the Z/E Isomers of Tetraphenylethene Derivatives: Stereoselective Synthesis, AIE Mechanism, Photophysical Properties, and Application as Chemical Probes

Deciphering Benzene–Heterocycle Stacking Interaction Impact on the Electronic Structures and Photophysical Properties of Tetraphenylethene-Cored Foldamers

Contact Info

Product

Resources

About