Photolability of Per-Arylated Butadienes: En Route to Dihydronaphthalenes

Freudenberg, Jan; Uptmoor, Andrea C.; Röminger, Frank; Bunz, Uwe H. F.

doi:10.1021/jo502293q

Cited by 15 publications

(5 citation statements)

References 22 publications

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“…We further noticed that HPB derivatives could undergo photoinduced cyclization to generate their cycloisomers, namely dihydronaphthalene (DHN). 19 Thus, there is a large possibility that the shorter-wavelength emission in the PL spectra of 5, P1a/2a, P1a/2b, and P3/4 arise from the DHN moieties in their backbones. With such presumption, the PL spectra of 5, P1a/2a, P1a/ 2b, and P1c/2a can be better explained.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…On the other hand, we noticed that the PL spectrum of tetraphenylethene (TPE) exhibited a similar phenomenon, and the emission at the bluer region was proved to be caused by its photocyclization in the presence of UV irradiation, producing 9,10-diphenylphenanthrene as the product. We further noticed that HPB derivatives could undergo photoinduced cyclization to generate their cycloisomers, namely dihydronaphthalene (DHN) . Thus, there is a large possibility that the shorter-wavelength emission in the PL spectra of 5 , P 1a/2a , P 1a/2b , and P 3/4 arise from the DHN moieties in their backbones.…”

Section: Resultsmentioning

confidence: 99%

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Aggregation-Induced Emission and Photocyclization of Poly(hexaphenyl-1,3-butadiene)s Synthesized from “1 + 2” Polycoupling of Internal Alkynes and Arylboronic Acids

et al. 2016

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A new polymerization method for in situ generation of luminescent polymers with aggregation-induced emission characteristics from readily prepared or commercially available reactants was developed in this work. The “1 + 2” polycoupling of internal alkynes and arylboronic acids took place under mild reaction conditions and was tolerant to moisture, air, and monomer stoichiometric imbalance, furnishing poly(hexaphenyl-1,3-butadiene)s (PHBs) with partially or wholly conjugated structures in satisfactory yields. All the PHBs showed good solubility, thermal stability, and film-forming ability. Their optical properties could be easily tuned by proper monomer design and external perturbation. The PHBs underwent active photocyclization in both solution and solid states, converting them to poly(dihydronaphthalene)s. Such a property made them promising materials for fabricating luminescent photopatterns. A new mechanistic pathway was proposed as supplementary to explain the aggregation-induced emission (AIE) phenomenon by studying the emission of PHBs and the corresponding model compound.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Aggregation-Induced Emission and Photocyclization of Poly(hexaphenyl-1,3-butadiene)s Synthesized from “1 + 2” Polycoupling of Internal Alkynes and Arylboronic Acids

et al. 2016

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“…HPBs are photoswitchable to dihydronaphthalenes, as shown in Figure A, in both solution and the solid state, even under anaerobic conditions. Additionally, the “1+2” polycoupling of internal alkynes and arylboronic acids takes place under mild reaction conditions and is tolerant to moisture, air, and monomer stoichiometric imbalance, furnishing poly(hexaphenyl‐1,3‐butadiene)s (PHPBs) with partially or wholly conjugated structures in satisfactory yields .…”

Section: Property Of Mpbsmentioning

confidence: 99%

“…A blank TLC plate is shown as a reference. (B) The polymer PHPB can be transformed into Cyclo‐PHPB in the presence of UV irradiation …”

Section: Property Of Mpbsmentioning

confidence: 99%

Aggregation‐Induced Emission of Multiphenyl‐Substituted 1,3‐Butadiene Derivatives: Synthesis, Properties and Application

Zhang

Mao

et al. 2018

Chemistry A European J

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Organic functional materials, including conjugated molecules and fluorescent dyes, have been intensely developed in recent years because they can be applied in many fields, such as solar cells, biosensing and bioimaging, and medical adjuvant therapy. Organic functional materials with aggregation-induced emission or aggregation-enhanced emission (AIE/AEE) characteristics have increasingly attracted attention due to their high quantum efficiency in the aggregated or solid state. A large variety of AIE/AEE materials have been designed and applied during the exponential growth of research interest in the abovementioned fields. Multiphenyl-substituted 1,3-butadiene (MPB), as a core structure that includes tetraphenyl-1,3-butadiene, hexaphenyl-1,3-butadiene and their derivatives, show a typical AIE/AEE feature and can be potentially used in all the above-mentioned fields. This review summarizes the design principles, the corresponding syntheses, and the structure-property relationships of MPBs, as well as their excellent innovative functionalities and applications. This review will be useful for scientists conducting chemistry, materials, and biomedical research in AIE/AEE-related fields.

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“…On the other hand, Miura and Satoh and coworkers developed the synthesis of 1,3‐butadiene derivatives from the reaction of internal alkynes with arylboronic acids ( Scheme 1 ,a ) [23,24] . Although AIE active 1,1,2,3,4,4‐hexaaryl‐1,3‐butadienes and their polymers have been also synthesized using Miura ’s method, [25–31] applications are limited probably because the reaction temperature is too high (120 °C) and because some 1,1,2,3,4,4‐hexaaryl‐1,3‐butadienes can easily be cyclized to produce 1,1,2,3,4‐pentaarylated dihydronaphthalenes [32] . Based on these backgrounds, herein, we disclose the simple modification to afford 1,1,2,3,4,4‐hexaaryl‐1,3‐butadienes under mild reaction conditions ( Scheme 1 ,b ).…”

Section: Introductionmentioning

confidence: 99%

Simple Modifications for the Facile Preparation of 1,1,2,3,4,4‐Hexaaryl‐1,3‐butadienes

Sakaguchi

Kusumoto

Shimomura

et al. 2022

Helvetica Chimica Acta

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A facile preparation of 1,1,2,3,4,4‐hexaaryl‐1,3‐butadienes which are important molecules due to their aggregation‐induced emission (AIE) activity was achieved by simple modifications of the reaction conditions reported in the previous work. In this reaction system, the insertion of alkynes into the palladium−carbon bond will be accelerated by changing the palladium intermediate to the cationic one. When silver nitrate was used, the reaction of diarylalkynes with arylboronic acids took place smoothly under mild reaction conditions without any ligand to give the coupling diene products in excellent yields. On the contrary, the reaction hardly proceeded with silver oxide and silver carbonate. Poly(hexaphenyl‐1,3‐butadiene) (PHB) with a similar molecular weight to the previously prepared one was also synthesized from the reaction of diphenylacetylene with phenyldiboronic acid under mild reaction conditions.

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Photolability of Per-Arylated Butadienes: En Route to Dihydronaphthalenes

Cited by 15 publications

References 22 publications

Aggregation-Induced Emission and Photocyclization of Poly(hexaphenyl-1,3-butadiene)s Synthesized from “1 + 2” Polycoupling of Internal Alkynes and Arylboronic Acids

Aggregation-Induced Emission and Photocyclization of Poly(hexaphenyl-1,3-butadiene)s Synthesized from “1 + 2” Polycoupling of Internal Alkynes and Arylboronic Acids

Aggregation‐Induced Emission of Multiphenyl‐Substituted 1,3‐Butadiene Derivatives: Synthesis, Properties and Application

Simple Modifications for the Facile Preparation of 1,1,2,3,4,4‐Hexaaryl‐1,3‐butadienes

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