Synthesis and characterization of AIE-active and photo-active α-cyanostilbene-containing carbazole-based hexacatenars

Zuo, Rongzhou; Wang, Shangwen; Pang, Yida; Xiao, Yulong; Jiang, Zonglin

doi:10.1016/j.dyepig.2021.109153

Cited by 32 publications

(4 citation statements)

References 92 publications

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“…Jiang et al created a biscyanovinyl diphenylcarbazole-based hexacatenar (37) in 2021, which was structurally characterised using 1 H NMR, 13 C NMR, and EA. The NH group served as the central core while cyanostilbene served as the functional group 91 (Fig. 25).…”

Section: Some Other Examples Of Carbazole Cyanostilbene Derivativesmentioning

confidence: 99%

Symphony of light: AIE and MFC in carbazole-based cyanostilbenes

Afrin,

Chinna Ayya Swamy

2024

J. Mater. Chem. C

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Section: Some Other Examples Of Carbazole Cyanostilbene Derivativesmentioning

confidence: 99%

Symphony of light: AIE and MFC in carbazole-based cyanostilbenes

Afrin,

Chinna Ayya Swamy

2024

J. Mater. Chem. C

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“…Previously, we combined the Einstein radiation transition formula with photoluminescence efficiency to illustrate the mechanism of DSE luminophores based on triphenylamine (TPA) at the quantum chemical level. Carbazole is similar to triphenylamine in chemical structure and is widely used as a basic unit for the construction of organic luminescent materials [20][21][22], but the obtained luminescent materials have either AIE activity [23,24] or effective luminescence in dilute solutions. Carbazole derivatives reported in recent literature, which can effectively emit in both solution and solid state, are still rare [25][26][27], especially those obtained from combining theoretical calculations and experimentally relevant literatures.…”

Section: Diarylmaleimides (Dams)mentioning

confidence: 99%

Preparation and Characterization of Carbazole-Based Luminogen with Efficient Emission in Solid and Solution States

Zhang,

Wei,

Tang

et al. 2023

Materials

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Organic luminescent materials with high luminescence efficiency in both solution and solid states, namely dual-state emission (DSE), have attracted considerable attention due to their promising applications in various fields. In order to enrich the variety of DSE materials, carbazole, similar to triphenylamine (TPA), was utilized to construct a novel DSE luminogen named 2-(4-(9H-carbazol-9-yl)phenyl)benzo[d]thiazole (CZ-BT). CZ-BT exhibited DSE characteristics with fluorescence quantum yields of 70, 38 and 75% in solution, amorphous and crystalline states, respectively. CZ-BT shows thermochromic and mechanochromic properties in solution and solids, respectively. Theoretical calculations show that there is a small conformational difference between the ground state and the lowest singly excited state of CZ-BT and that it exhibits a low non-radiative transition characteristic. The oscillator strength during the transition from the single excited state to the ground state reaches 1.0442. CZ-BT adopts a distorted molecular conformation with intramolecular hindrance effects. The excellent DSE properties of CZ-BT can be explained well using theoretical calculations and experimental results. In terms of application, the CZ-BT has a detection limit for the hazardous substance picric acid of 2.81 × 10−7 mol/L.

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“…[17][18][19][20][21] Unlike a fantastic AIE report on the tetraphenylethene molecular system, relatively little α-cyanostilbene, bis-cyanostilbene and their analogues were investigated for AIE research. [22][23][24][25][26] The α-cyanostilbene and bis-cyanostilbene are chromophoric molecular systems which could easily engineer via incorporation of electron-donating and or electron-withdrawing substituents, adding aromatic rings. The careful molecular engineering of αcyanostilbene and bis-cyanostilbene core enhances their πconjugation length which would leads to high fluorescence intensity and large stokes shift.…”

Section: Introductionmentioning

confidence: 99%

“…A review of the literature revealed that very few scientific papers reported how systematic modifications in π‐conjugation length of small organic compounds affected on their aggregation induced emission (AIE) properties [17–21] . Unlike a fantastic AIE report on the tetraphenylethene molecular system, relatively little α‐cyanostilbene, bis‐cyanostilbene and their analogues were investigated for AIE research [22–26] . The α‐cyanostilbene and bis‐cyanostilbene are chromophoric molecular systems which could easily engineer via incorporation of electron‐donating and or electron‐withdrawing substituents, adding aromatic rings.…”

Section: Introductionmentioning

confidence: 99%

Assessing the Impact of π‐Conjugation Length on Aggregation Induced Emission and Self‐Assembly Formation of α‐Cyanostilbene and Bis‐Cyanostilbene

Waghchoure,

Narode,

Sangale

et al. 2024

ChemistrySelect

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In this work, short π‐conjugated (Z)‐2‐(4‐(2‐cyano‐2‐phenylvinyl)phenoxy)‐N‐(1‐(3‐ethoxy‐4‐methoxyphenyl)‐2‐(methyl sulfonyl)ethyl)acetamide (CYS) and large π‐conjugated 2,2′‐(((1Z,1′Z)‐1,4‐phenylenebis(2‐cyanoethene‐2,1‐diyl))bis(4,1‐phenyl ene))bis(oxy))bis(N‐(1‐(3‐ethoxy‐4‐methoxyphenyl)‐2‐(methyl sulfonyl)ethyl)acetamide (BCYS) compounds were synthesized. Furthermore, the influence of π‐conjugation length on CYS and BCYS absorption, fluorescence, aggregation induced emission (AIE) characteristics, and self‐assembly was examined. The large π‐conjugated BCYS (π‐conjugation length=18.71 Å) exhibits AIE property getting on in the DMSO−Water solvent combination as the volume % of water increases and demonstrated production of self‐assembled bundle of micro fibrous structure of around 5 to 6 microns long and 200 to 500 nm wide. Short π‐conjugated CYS (π‐conjugation length=10.80 Å), on the other hand, exhibits aggregation caused quenching (ACQ) in the DMSO−Water solvent combination as the volume % of water increases and the creation of self‐assembled nanostructured crystalline asymmetrical particles. Moreover, the cytotoxicity study of CYS and BCYS revealed that BCYS had superior biocompatibility than CYS.

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Synthesis and characterization of AIE-active and photo-active α-cyanostilbene-containing carbazole-based hexacatenars

Cited by 32 publications

References 92 publications

Symphony of light: AIE and MFC in carbazole-based cyanostilbenes

Symphony of light: AIE and MFC in carbazole-based cyanostilbenes

Preparation and Characterization of Carbazole-Based Luminogen with Efficient Emission in Solid and Solution States

Assessing the Impact of π‐Conjugation Length on Aggregation Induced Emission and Self‐Assembly Formation of α‐Cyanostilbene and Bis‐Cyanostilbene

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