Energy-level tuning of poly(p-phenylenebutadiynylene) derivatives by click chemistry-type postfunctionalization of side-chain alkynes

Wang, Dong; Gao, Hong; Wang, Xiangke; Yang, Zhou; He, Wanli; Cao, Hui; Gu, Jianming; Hu, Huiying; Yang, Huai

doi:10.1016/j.reactfunctpolym.2016.06.001

Cited by 10 publications

(3 citation statements)

References 57 publications

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“…As TCNE was added, the absorption peak for P at 384 nm gradually weakened, and a new weak peak for compounds P-1 , P-11 and P-111 appeared at 478 nm. According to previous literature, 28–34 the click chemical reaction is fast and quantitative, and the peak intensity in previous work was linearly related to the titration volume. Compound P has three clickable alkynyl groups; after adding TCNE solution, four compounds ( P , P-1 , P-11 and P-111 ) coexisted, and the ratio of P , P-1 , P-11 and P-111 was not definite.…”

Section: Resultsmentioning

confidence: 86%

Click reactions to prepare symmetrical and asymmetrical and broad-band near-infrared absorbing dyes

Zhao

Song

et al. 2023

New J. Chem.

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Section: Resultsmentioning

confidence: 86%

Click reactions to prepare symmetrical and asymmetrical and broad-band near-infrared absorbing dyes

Zhao

Song

et al. 2023

New J. Chem.

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“…On the whole, the absorption intensities of the precursor (R) at 384 nm started to decrease, while the absorption intensities of the new compounds at 470 nm increased gradually. In the previous work (Wang et al, 2016a(Wang et al, , 2016bMiao et al, 2016;Wang et al, 2016aWang et al, , 2016b, it had been proved that the click chemistry reaction was quick and quantitative, and the linear changing relationship between peak intensity and titration volume was observed. In this experiment, the compound R had three clicked alkynyl groups, and three kinds of compounds (R, R-1, R-11 and R-111) coexisted after the TCNE solution was added.…”

Section: Uv-vis-nir Spectroscopymentioning

confidence: 95%

Nonlinear optical properties of symmetrical and asymmetrical benzene derivatives with click chemistry modification

Zhao

Zhang

et al. 2023

PRT

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Purpose This paper aims to prepare third-order nonlinear optical (NLO) organic materials with large nonlinear optimization value, high damage threshold and ultrafast response time. Design/methodology/approach A series of novel symmetric and asymmetric compounds possessing third-order NLO properties were synthesized using 1,3,5-tribromobenzene as the basis. The photophysical and electrochemical properties, as well as the click reactions, were characterized by means of UV–VIS–NIR absorption spectroscopy and cyclic voltammetry. Findings The donor–acceptor chromophores were inserted into compound, making the molecule to have a broader absorption in the near-infrared regions and a narrower optical and electrochemical band gap. It also formed an electron-delocalized organic system, which has larger effects on achieving a third-order NLO response. The third-order NLO phenomenon of benzene ring complexes was experimentally studied at 532 nm using Z-scan technology, and some compounds showed the expected NLO properties. Originality/value The click products exhibit more NLO phenomena by performing different click combinations to the side groups, opening new perspectives on using the system in a variety of photoelectric applications.

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“…The discovery of new photoacoustic molecular materials has been restricted by the paucity of systematic studies on factors affecting PA effects, which has led to poor guidance in the study of molecular photoacoustic contrast agent design [ 4 , 15 , 16 ]. Lately, the chemistry of [2 + 2] cycloaddition-cycloreversion reactions between tetracyanoethylene (TCNE), 7,7,8,8-tetracyanodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanodimethane (F 4 -TCNQ) and ‘electronically chaotic’ alkynes were focused on [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ]. The consequent adducts, specifically those composed of F 4 -TCNQ formation, had excellent solubility and could be easily produced in high yields.…”

Section: Introductionmentioning

confidence: 99%

Photoacoustic Effect of Near-Infrared Absorbing Organic Molecules via Click Chemistry

et al. 2022

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Near-infrared dyes were developed to be contrast agents due to their ability to improve the productivity of photoacoustic (PA) imaging and photothermal therapy (PTT) treatments. During the article, we described in detail the PA and PT effects of a category of organic molecules. F4-TCNQ could potentially cause a red-shift in the peak PA intensity. The results show that the PTT intensity of the near-infrared dyes with phenyl groups were higher than near-infrared dyes with thiophene groups. We also investigated the photodynamic treatment effect of C1b to demonstrate that these dyes are highly desirable in biochemistry. The high photoacoustic intensity of the organic molecules and the good yield of reactive oxygen species could indicate that these dyes have good potential for a wide range of imaging applications. Finally, we embedded the dye (C1b) in a liposomal hydrophobic phospholipid bilayer (C1b⊂L) to facilitate the application of hydrophobic dyes in biomedical applications, which can be absorbed by cells with good compatible and high stability for the imaging of cellular PA.

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Energy-level tuning of poly(p-phenylenebutadiynylene) derivatives by click chemistry-type postfunctionalization of side-chain alkynes

Cited by 10 publications

References 57 publications

Click reactions to prepare symmetrical and asymmetrical and broad-band near-infrared absorbing dyes

Click reactions to prepare symmetrical and asymmetrical and broad-band near-infrared absorbing dyes

Nonlinear optical properties of symmetrical and asymmetrical benzene derivatives with click chemistry modification

Photoacoustic Effect of Near-Infrared Absorbing Organic Molecules via Click Chemistry

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