Practical Synthesis of Unsymmetrical Tetraarylethylenes and Their Application for the Preparation of [Triphenylethylene−Spacer−Triphenylethylene] Triads

Banerjee, Mohua; Emond, Susanna J.; Lindeman, Sergey V.; Rathore, Rajendra

doi:10.1021/jo701474y

Cited by 105 publications

(67 citation statements)

References 48 publications

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“…[21] Compounds 2 and 3 were synthesized according to the literature method. [22][23][24] 1,3,3-Trimethylindolino-7'-bromobenzopyrylospiran (1 a Synthesis of 1-(4-vinylphenyl)-l,2,2-triphenylethylene (4) 4-(1,2,2-Triphenylvinyl)benzaldehyde (3) (3.6 g, 10 mmol) and methyltriphenylphosphonium bromide (4.3 g, 12 mmol) were dissolved in THF (15 mL) and THF (25 mL) solution containing potassium tertbutoxide (1.68 g, 15 mmol) was slowly added dropwise at 0 8C under a N 2 atmosphere. The reaction went on for 10 h. Then the reaction mixture was quenched with the addition of a saturated aqueous solution of sodium chloride (10 mL).…”

Section: Synthesis and Characterizationsmentioning

confidence: 99%

Reversible Multistimuli‐Response Fluorescent Switch Based on Tetraphenylethene–Spiropyran Molecules

Qian

et al. 2014

Chemistry A European J

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Two tetraphenylethene (TPE)-functionalized spiropyran (SP) molecules with very similar structure were designed and synthesized. The two molecules exhibit aggregation-induced emission (AIE) properties, as well as multistimuli-responsive color-changing properties, such as photochromism and acidchromism. The investigation of their different photochromic and acidchromic characteristics and dual-response fluorescent switch during isomerization indicated that the different link position between TPE and SP will significantly affect the extended π-conjugated system, resulting in completely different photochromic and acidchromic properties.

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Section: Synthesis and Characterizationsmentioning

confidence: 99%

Reversible Multistimuli‐Response Fluorescent Switch Based on Tetraphenylethene–Spiropyran Molecules

Qian

et al. 2014

Chemistry A European J

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“…The detailed procedures for the syntheses of the reaction intermediates and final products are described in the Supporting Information and Experimental section. Briefly, 2 was prepared as a key intermediate in high yield by lithiation of 4, [12] followed by treatment with trimethyl borate and hydrolysis catalyzed by acid.…”

mentioning

confidence: 99%

Changing the Behavior of Chromophores from Aggregation‐Caused Quenching to Aggregation‐Induced Emission: Development of Highly Efficient Light Emitters in the Solid State

et al. 2010

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“…For asymmetric ethenes, Banerjee et al proposed an effective method which is based on the reaction of diphenylmethyllithium and diaryl ketone. 33 The other method is the famous McMurry coupling in which the diaryl ketone can be catalyzed by zinc powder and TiCl 4 to afford the symmetric ethenes. 34,35 In the two methods, it is obvious that the intermediate ketones play an important role in deciding the structures of the products.…”

Section: Synthesismentioning

confidence: 99%

A series of 4,5,9,10-tetrahydropyrene-based tetraarylethenes: synthesis, structures and solid-state emission behavior

et al. 2018

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By controlling the number of 4,5,9,10-tetrahydropyrene segments around the tetraarylethene core, a series of 4,5,9,10-tetrahydropyrene-based tetraarylethenes were synthesized and structurally characterized. An aggregation-induced emission (AIE) study indicated that all the compounds are AIE active: they are weak emitters in good solvents but highly emissive in the condensed phase, and hence are potential solidstate emitters. Their optical properties, electrochemical properties and theoretical calculations were investigated, and the results prove that the p-conjugation degree of these compounds increases with the increasing number of 4,5,9,10-tetrahydropyrene units. However, the fluorescence quantum yield in the solid state doesn't increase with increasing p-conjugation. We studied the reason for this by analyzing the crystal structures of some compounds, and proposed that the close degree of molecular packing in the solid state may be responsible for it. Loose packing of tetraarylethenes in the solid state can restrict the rotation of the aromatic rings but cannot constrain other non-radiative pathways efficiently, such as vibration, which leads to the unpredictable emission of the compounds. IntroductionThe design and synthesis of organic materials with efficient solid-state uorescence has attracted extensive attention because the performance of organic photoelectric devices is usually dependent on the solid-state properties of materials. 1-4And most luminogenic molecules, especially those with disclike shapes, normally exhibit quenched emission in the condensed state due to the formation of intermolecular pstacking interactions.5-7 Several strategies have been developed to solve this problem such as designing polymers with dendritic structures and using antiaggregation reagents to modulate aggregation. [8][9][10] In these methods, the design ideas are obstructing the formation of luminophoric aggregates. Recently, it has been proved that the construction of organic compounds with aggregation-induced emission property is a convenient but effective way to obtain outstanding luminogens.11-16 Different from the ordinary organic compounds usually with excellent single-molecule emission in solvents, AIE compounds are weakly emissive in good solvent but they become strong emitters when the condensed phase are formed. 17In aggregates, intramolecular rotation which acts as a nonradiative pathway can be restricted effectively, meanwhile the twisted structure of these compounds can avoid the formation of p-stacking to a certain extent, thus achieving high solid-state emission efficiency. As a representative member of AIE dyes, tetraphenylethene (TPE) has attracted much research attention because it enjoys the advantages such as efficient solid-state emission, facile synthesis and easy functionalization.18-20 In addition, by combing TPE and many kinds of polycyclic aromatic hydrocarbons (PAHs), a large number of novel TPE derivatives have been developed. [21][22][23][24][25][26][27] It has been reported that the uores-c...

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Practical Synthesis of Unsymmetrical Tetraarylethylenes and Their Application for the Preparation of [Triphenylethylene−Spacer−Triphenylethylene] Triads

Cited by 105 publications

References 48 publications

Reversible Multistimuli‐Response Fluorescent Switch Based on Tetraphenylethene–Spiropyran Molecules

Reversible Multistimuli‐Response Fluorescent Switch Based on Tetraphenylethene–Spiropyran Molecules

Changing the Behavior of Chromophores from Aggregation‐Caused Quenching to Aggregation‐Induced Emission: Development of Highly Efficient Light Emitters in the Solid State

A series of 4,5,9,10-tetrahydropyrene-based tetraarylethenes: synthesis, structures and solid-state emission behavior

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