7, 8-Dichlorobenzo[ghi]perylenetriimide: A versatile synthon for bay-substituted π-extended perylene dyes

Li, Lei; Zhu, Junyang; Hong, Yu-Jian; Li, Menghua; Xiao, Weiping; Lin, Mei‐Jin

doi:10.1016/j.dyepig.2019.04.019

Cited by 10 publications

(3 citation statements)

References 49 publications

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“…It was speculated that the substituted chlorine on CTC might be a good leaving group because of the easy fracture of C-X (Cl). [35][36][37] Therefore, CTC could easily form covalent bonds with MRFNs (existing hydroxyl, carboxyl groups, and possibly amino groups) with a high affinity. On the one hand, with an increase in the rigidity of the molecular structure, the energy loss produced by the excited electrons state returning to the ground state was reduced; on the other hand, the self-complexation of MRFNs might be broken, which could reduce the aggregation of MRFNs molecules, so the dispersion state between MRFNs molecules was maintained, thus enhancing the uorescence of MRFNs.…”

Section: Possible Mechanisms For Tc-induced Uorescence Quenching Andmentioning

confidence: 99%

Novel methods for the rapid detection of trace tetracyclines based on the fluorescence behaviours of Maillard reaction fluorescent nanoparticles

Wang

et al. 2020

RSC Adv.

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Section: Possible Mechanisms For Tc-induced Uorescence Quenching Andmentioning

confidence: 99%

Novel methods for the rapid detection of trace tetracyclines based on the fluorescence behaviours of Maillard reaction fluorescent nanoparticles

Wang

et al. 2020

RSC Adv.

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“…Polycyclic aromatic hydrocarbons (PAHs) containing imide groups have attracted considerable attention from organic and material chemists due to their interesting electronic structures and absorption and emission properties. For instance, imide derivatives based on PAHs, such as perylene and coronene, exhibit unique optical, [1][2][3][4][5][6] photophysical, [7][8][9][10][11][12][13][14][15] and supramolecular [16][17][18][19][20][21][22] properties. The electron mobility of pyrene-, [23,24] tetracene-, [25] pentacene-, [25] and hexacene- [26] based diimides which show the low-lying LUMO levels due to the imide units, were evaluated for n-type organic field-effect transistors.…”

Section: Introductionmentioning

confidence: 99%

Fluorosolvatochromic Behavior of 2,3‐Naphthalimides Expanded by Double Fusion with Benzothiophene and Benzofuran Units

2023

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As new polycyclic aromatic hydrocarbons (PAHs) containing an imide group, we designed and synthesized 2,3‐naphthalimide fused with benzothiophene 1 or benzofuran 2. 1 and 2 have a push‐pull structure attributed to the imide group and the electron‐donating heterocyclic moieties, indicated that 1 and 2 play as a fluorosolvatochromic dye. 1 and 2 were synthesized in 3‐steps. The absorption and fluorescence spectra were measured in twelve different solvents. The absorption spectra of 1 and 2 showed a slight solvent dependence. On the other hand, a strong solvent dependence was observed in the fluorescence spectra of 1 and 2, that is, fluorosolvatochromism. The plots of the emission maximum versus the solvent polarity parameter ET(30) for 1 and 2 exhibited a good linear correlation. Multiple linear regression analysis using Catalán scale suggested that the fluorescence behavior of 1 and 2 is influenced by the acidity and dipolarity of the solvents. The changes in the dipole moment between the ground and excited states estimated by the Lippert‐Mataga equation were 7.6 D for 1 and 7.2 D for 2.

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“…In particular, nanoscale PDI‐self‐assemblies exhibit unique structural properties such as intrinsic π‐π stacking, dipole–dipole interactions, fast internal charge transfer, band‐like electronic structure, flexible structural modifiability, and well‐defined morphological adjustability 14 . The remarkable properties of PDI and its derivatives have made them significantly an important class of materials not only in synthetic chemistry but in the development of industrial dyes 15 …”

Section: Introductionmentioning

confidence: 99%

Living ring‐opening metathesis polymerization of norbornenes bay‐functionalized perylene diimides

Podiyanachari

Barłóg

Comí

et al. 2021

Journal of Polymer Science

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Ring‐opening metathesis polymerization (ROMP)‐derived poly(oxanorbornene imide)s bearing bay‐linked mono‐alkoxy‐M1 and 1,7‐di‐alkoxy M2 functionalized perylene diimides (PDIs) were synthesized using Grubb's third (G3) and Hoveyda‐Grubbs second generation (HG2) ruthenium‐alkylidene metathesis initiators. The mono‐alkoxy‐derived PDI‐based non‐ladderphane polymer polyM1 displayed 67% to 77% of the trans olefin content in the polymer chain depending on the initiator used for the polymerization. When using the symmetrical 1,7‐di‐alkoxy‐derived PDI‐based polymer polyM2 having the ladderphane type‐structure, this displayed a significant amount of cis and trans olefin contents in the polymer chains, irrespective of the type of initiators used for the polymerization. ROMP of both monomers M1 and M2 proceeded in a well‐controlled manner with a linear dependence of molecular weight on the monomer/initiator ratio using G3 as initiator. Optical properties of the ladderphane‐based polyM2 and non‐ladderphane‐based polyM1 were characterized in both solution and the film state. X‐ray diffraction (XRD) analysis for all the polymers showed significant π‐stacking in the thin film state with ordered molecular packing and closer values of d‐spacing for both polyM1 and polyM2. Film morphology examined by AFM elucidated homogenous smooth polymer surface for both polymers in general, but with some irregularities observed for polyM1. In addition, CV analysis revealed both polymers could be good candidates as electron‐accepting materials, with excellent film‐forming ability, and thermal stability.

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7, 8-Dichlorobenzo[ghi]perylenetriimide: A versatile synthon for bay-substituted π-extended perylene dyes

Cited by 10 publications

References 49 publications

Novel methods for the rapid detection of trace tetracyclines based on the fluorescence behaviours of Maillard reaction fluorescent nanoparticles

Novel methods for the rapid detection of trace tetracyclines based on the fluorescence behaviours of Maillard reaction fluorescent nanoparticles

Fluorosolvatochromic Behavior of 2,3‐Naphthalimides Expanded by Double Fusion with Benzothiophene and Benzofuran Units

Living ring‐opening metathesis polymerization of norbornenes bay‐functionalized perylene diimides

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