Molecular Association-Induced Emission Shifts for <i>E</i>/<i>Z</i> Isomers and Selective Sensing of Nitroaromatic Explosives

Hurlock, Matthew J.; Kan, Yuwei; Lécrivain, Thibaut; Lapka, Joseph L.; Nash, Kenneth L.; Zhang, Qiang

doi:10.1021/acs.cgd.8b01065

Cited by 17 publications

(15 citation statements)

References 45 publications

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“…This result would be favorable in terms of device applications. The lower Φ F, solid value of 10 b may be attributed to excimer formation in the solid state, as previously observed in the AIE‐active molecule with the same C=C unit, which is vicinally diarylated with p ‐NCC 6 H 4 [39] …”

Section: Resultssupporting

confidence: 64%

Stepwise Suzuki−Miyaura Cross‐Coupling of Triborylalkenes Derived from Alkynyl−B(dan)s: Regioselective and Flexible Synthesis of Tetrasubstituted Alkenes

et al. 2020

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Alkenes with three boryl groups of differing reactivities were synthesized and subsequently cross‐coupled regioselectively with aryl halides in a stepwise manner to afford tetrasubstituted alkenes. The key triborylalkene is derived from the platinum‐catalyzed diboration of alkynyl−B(dan)s with B2(pin)2. Due to excellent regioselectivity and reaction efficiency of each step starting with alkynyl−B(dan)s, tetrasubstituted alkenes with desired carbon frameworks at desired positions can be prepared in high yields. For example, an alkene with four distinct aryl groups, p‐MeOC6H4, p‐CF3C6H4, p‐MeC6H4, and p‐NCC6H4, was obtained in 71% overall yield via six steps, starting with the dehydrogenative borylation of p‐MeC6H4C≡CH with HB(dan). Moreover, a variety of tetrasubstituted alkenes, including regio‐ and stereoisomers of the above tetraarylalkene, AIE‐active TPTPE and derivatives thereof, and (Z)‐tamoxifen, a well‐known breast cancer drug, were accessed via the developed strategy.

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Section: Resultssupporting

confidence: 64%

Stepwise Suzuki−Miyaura Cross‐Coupling of Triborylalkenes Derived from Alkynyl−B(dan)s: Regioselective and Flexible Synthesis of Tetrasubstituted Alkenes

et al. 2020

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“…Once again, the difference in polarity between the Z and E isomersw as sufficient to allow their separation by column chromatography and the isomers were characterized by single-crystal X-ray diffraction (Figure 9a). [58] The absorption bands of the resultant( Z)-TPECN and (E)-TPECNc ompoundsw ere similart oo ne another (l % 275 and 315 nm, respectively). However,u nlike conventional TPE derivatives, (Z)-TPECN and (E)-TPECN exhibited uniqueA IE characteristics.…”

Section: Development Of Z/e Isomers Of Tpe Derivativesmentioning

confidence: 82%

“…introduced polar electron‐withdrawing cyano groups onto the TPE scaffold. Once again, the difference in polarity between the Z and E isomers was sufficient to allow their separation by column chromatography and the isomers were characterized by single‐crystal X‐ray diffraction (Figure a) . The absorption bands of the resultant ( Z )‐TPECN and ( E )‐TPECN compounds were similar to one another ( λ ≈275 and 315 nm, respectively).…”

Section: Development Of Z/e Isomers Of Tpe Derivativesmentioning

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

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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.

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“…Therefore, the EZI process has been studied with unsymmetrically disubstituted TPE derivatives [6][7][8][9][10][11][12][13][14][15][16][17]. Apart from being ideal candidates for the study of the EZI process, pure E-and Z-isomers of disubstituted TPE and the investigation of their properties has recently attracted interest based on the differences in their optical properties, host-guest chemistry and related features [18][19][20][21][22][23][24][25][26][27][28]. Disubstituted TPE derivatives are conventionally synthesized by the McMurry coupling of unsymmetrically sybstituted ketones.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced E to Z isomerization of tetraphenylethylene derivatives within organometallic supramolecular assemblies

Liu

et al. 2021

Sci. China Chem.

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Isolation of E-1,2-bis(4-bromophenyl)-1,2-diphenyl-ethylene from the E/Z isomer mixture obtained by a McMurry coupling reaction and reaction of this isomer with imidazole followed by N-alkylation with nBuBr and anion exchange yielded the bisimidazolium tetraphenylethylene (TPE) derivative H2-E-1(PF6)2. The reaction of H2-E-1(PF6)2 with Ag2O yielded the di-nuclear metallarectangle [Ag2(E-1)2](PF6)2 where the two bis-NHC donors E-1 bridge two silver atoms. Irradiation of [Ag2(E-1)2](PF6)2 leads to E/Z isomerization of the di-NHC ligand and formation of Z-1 in the mononuclear complex [Ag(Z-1)]PF6. Demetallation of the di-NHC ligand with NH4Cl/NH4PF6 yielded bisimidazolium salt H2-Z-1(PF6)2. The unique isomerization of the E-TPE derivative into its Z-isomer via metal complex formation/irradiation/demetallation cannot be achieved by irradiation of the individual imidazolium salt. The emissive properties of the TPE complexes [Ag2(E-1)2](PF6)2 and [Ag(Z-1)]PF6 have been investigated.

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Molecular Association-Induced Emission Shifts for E/Z Isomers and Selective Sensing of Nitroaromatic Explosives

Cited by 17 publications

References 45 publications

Stepwise Suzuki−Miyaura Cross‐Coupling of Triborylalkenes Derived from Alkynyl−B(dan)s: Regioselective and Flexible Synthesis of Tetrasubstituted Alkenes

Stepwise Suzuki−Miyaura Cross‐Coupling of Triborylalkenes Derived from Alkynyl−B(dan)s: Regioselective and Flexible Synthesis of Tetrasubstituted Alkenes

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

Photoinduced E to Z isomerization of tetraphenylethylene derivatives within organometallic supramolecular assemblies

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