Mechanoresponsive Material of AIE-Active 1,4-Dihydropyrrolo[3,2-b]pyrrole Luminophores Bearing Tetraphenylethylene Group with Rewritable Data Storage

Ma, Yu‐Qing; Zhang, Yuyang; Kong, Lin; Yang, Jiaxiang

doi:10.3390/molecules23123255

Cited by 21 publications

(16 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“… 13 This situation changed dramatically in 2013, when we serendipitously found a method that allows rapid access to 1,4-dihydro-tetraarylpyrroles[3,2- b ]pyrroles (TAPPs). 14 Since then, TAPPs have found multiple applications in research related to studying symmetry-breaking in the excited state, 15 two-photon absorption, 16 solvatofluorochromism, 13c , 13d direct solvent probing via H-bonding interactions, 17 photochromic analysis of halocarbons, 18 organic field-effect transistors, 19 dye-sensitized solar cells, 20 bulk heterojunction organic solar cells, 21 organic light-emitting diodes, 22 resistive memory devices, 23 aggregation-induced emission, 24 and MOFs. 25 It has been also shown that TAPPs are an excellent platform for the synthesis of the π-expanded heteroanalogues of polycyclic aromatic hydrocarbons.…”

Section: Introductionmentioning

confidence: 99%

Method for the Large-Scale Synthesis of Multifunctional 1,4-Dihydro-pyrrolo[3,2-b]pyrroles

et al. 2020

View full text Add to dashboard Cite

A thorough investigation has enabled the optimization of the synthesis of 1,4-dihydro-pyrrolo[3,2- b ]pyrroles. Although salts of such metals as vanadium, niobium, cerium, and manganese were found to facilitate the formation of 1,4-dihydro-pyrrolo[3,2- b ]pyrroles from amines, aldehydes, and diacetyl, we confirmed that iron salts are the most efficient catalysts. The conditions identified (first step: toluene/AcOH = 1:1, 1 h, 50 °C; second step: toluene/AcOH = 1:1, Fe(ClO 4 ) 3 ·H 2 O, 16 h, 50 °C) resulted in the formation of tetraarylpyrrolo[3,2- b ]pyrroles in a 6–69% yield. For the first time, very electron-rich substituents (4-Me 2 NC 6 H 4 , 3-(OH)C 6 H 4 , pyrrol-2-yl) originating from aldehydes and sterically hindered substituents (2-ClC 6 H 4 , 2-BrC 6 H 4 , 2-CNC 6 H 4 , 2-(CO 2 Me)C 6 H 4 , 2-(TMS-C≡C)C 6 H 4 ) present on anilines can be appended to the pyrrolo[3,2- b ]pyrrole core. It is now also possible to prepare 1,4-dihydropyrrolo[3,2- b ]pyrroles bearing an ordered arrangement of N -substituents and C -substituents ranging from coumarin, quinoline, phthalimide to truxene. These advances in scope enable independent regulations of many desired photophysical properties, including the Stokes shift value and emission color ranging from violet-blue through deep blue, green, yellow to red. Simultaneously, the optimized conditions have finally allowed the synthesis of these extremely promising heterocycles in amounts of more than 10 g per run without a concomitant decrease in yield or product contamination. Empowered with better functional group compatibility, novel derivatization strategies were developed.

show abstract

Section: Introductionmentioning

confidence: 99%

Method for the Large-Scale Synthesis of Multifunctional 1,4-Dihydro-pyrrolo[3,2-b]pyrroles

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Then the letters “DCM” could be written with a stick and be wiped off by swabbing or heating measures ( Figure 3 d). 39 …”

Section: Resultsmentioning

confidence: 99%

Development of a New Multiple Stimuli-Responsive Fluorescent Material Using the Minus Strategy Based on the Structure of Tetraphenyl-1,3-butadiene

Lin

Wang

et al. 2022

ACS Omega

View full text Add to dashboard Cite

In this study, we designed and synthesized a new class of aggregation-induced emission luminogens, which was inspired and developed from the structure of tetraphenyl-1,3-butadienes derivative (TPB-1) through the minus strategy by removing one of the phenyl groups. Among them, L1 and L4 exhibited an aggregation-induced emission effect and multistimuli-responsive chromic behavior. Moreover, two types of single crystals of L1 were obtained, and their different emission behaviors were elucidated clearly by analyzing the single-crystal data.

show abstract

“…Then, the fluorescent letters could be easily erased by fuming with DCM for a few minutes; after that, the letters could be rewritten with a rod and wiped off again, and the writing/erasing process could be repeated many times. Therefore, this material shows great potential for applications on rewritable paper [ 40 ].…”

Section: Resultsmentioning

confidence: 99%

Achieving Molecular Fluorescent Conversion from Aggregation-Caused Quenching to Aggregation-Induced Emission by Positional Isomerization

Wang

Lin

et al. 2021

Molecules

View full text Add to dashboard Cite

In this work, we synthesized a pair of positional isomers by attaching a small electron-donating pyrrolidinyl group at ortho- and para-positions of a conjugated core. These isomers exhibited totally different fluorescent properties. PDB2 exhibited obvious aggregation-induced emission properties. In contrast, PDB4 showed the traditional aggregation-caused quenching effect. Their different fluorescent properties were investigated by absorption spectroscopy, fluorescence spectroscopy, density functional theory calculations and single-crystal structural analysis. These results indicated that the substituent position of the pyrrolidinyl groups affects the twisted degree of the isomers, which further induces different molecular packing modes, thus resulting in different fluorescent properties of these two isomers. This molecular design concept provided a new accurate strategy for designing new aggregation-induced emission luminogens.

show abstract

Mechanoresponsive Material of AIE-Active 1,4-Dihydropyrrolo[3,2-b]pyrrole Luminophores Bearing Tetraphenylethylene Group with Rewritable Data Storage

Cited by 21 publications

References 58 publications

Method for the Large-Scale Synthesis of Multifunctional 1,4-Dihydro-pyrrolo[3,2-b]pyrroles

Method for the Large-Scale Synthesis of Multifunctional 1,4-Dihydro-pyrrolo[3,2-b]pyrroles

Development of a New Multiple Stimuli-Responsive Fluorescent Material Using the Minus Strategy Based on the Structure of Tetraphenyl-1,3-butadiene

Achieving Molecular Fluorescent Conversion from Aggregation-Caused Quenching to Aggregation-Induced Emission by Positional Isomerization

Contact Info

Product

Resources

About