1,6- and 1,7-Regioisomers of Asymmetric and Symmetric Perylene Bisimides: Synthesis, Characterization and Optical Properties

Tsai, Hsing-Yang; Chang, Che-Wei; Chen, Kew‐Yu

doi:10.3390/molecules19010327

Cited by 20 publications

(12 citation statements)

References 73 publications

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“…Under the same conditions, and only by carrying out the reaction for a longer time (6 h), the bis-nitration can occur to afford the two regioisomers (1,6)-and (1,7)-dinitroPDI 4 with no, or almost no selectivity [52]. Notably, when the reaction was described in the presence of CAN for 48 h, the authors claimed a selectivity in favor of the regioisomer (1,7) 4b (3:1) and the possibility of separating the two regioisomers by HPLC or repetitive crystallizations [40,53].…”

Section: Nucleophilic Substitution Of the Nitro Groupmentioning

confidence: 99%

Nitro-Perylenediimide: An Emerging Building Block for the Synthesis of Functional Organic Materials

2020

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Perylenediimide (PDI) is one of the most important classes of dyes and is intensively explored in the field of functional organic materials. The functionalization of this electron-deficient aromatic core is well-known to tune the outstanding optoelectronic properties of PDI derivatives. In this respect, the functionalization has been mostly addressed in bay-positions to halogenated derivatives through nucleophilic substitutions or metal-catalyzed coupling reactions. Being aware of the synthetic difficulties of obtaining the key intermediate 1-bromoPDI, we will present as an alternative in this review the potential of 1-nitroPDI: a powerful building block to access a large variety of PDI-based materials.

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Section: Nucleophilic Substitution Of the Nitro Groupmentioning

confidence: 99%

Nitro-Perylenediimide: An Emerging Building Block for the Synthesis of Functional Organic Materials

2020

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“…The results may account for the fact that the 1,7-regioisomer has a more extended effective conjugation length than the 1,6-regioisomer. 32,33 Figure 6 shows the highest occupied molecular orbitals (HOMOs) and the lowest unoccupied molecular orbitals (LUMOs) of 1 and 2. The HOMO of both compounds is delocalized mainly on the amino group and the perylene core, while the LUMO is extended from the central perylene core to the bisimide groups.…”

Section: Compound 1 Possesses Two Intramolecular C-h• • • N Hydrogen mentioning

confidence: 99%

“…However, only a few reports of isolation and characterization of both 1,6-and 1,7-disubstituted PBIs have been reported, and still very little is known about the molecular structures and spectroscopic properties of 1,6-disubstituted PBIs. 31 33 To reveal the structure-property relationship of PBI molecules, we herein report the single-crystal X-ray diffraction structure and complementary density functional * For correspondence theory (DFT) calculations of 1,6-diaminoperylene bisimide (1). The results offer the potential to synthesize 1,6-disubstituted PBIs with extended molecular architectures and photophysical properties.…”

Section: Introductionmentioning

confidence: 99%

1,6-Diaminoperylene bisimide with a highly twisted perylene core

Chang

Chien

et al. 2017

J Chem Sci

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1,6-Diaminoperylene bisimide (1) was synthesized and characterized by single-crystal X-ray diffraction. To the best of our knowledge, this is the first time that the structure of 1,6-disubstituted perylene bisimide has been reported. The crystal belongs to triclinic, space group P-1, with a = 10.3966(10), b = 15.3398(16), c = 16.8495(17) Å, α = 79.490(4) • , β = 87.055(3) • , γ = 79.423(3) • , and Z = 2. Compound 1 possesses two intramolecular C-H• • • N hydrogen bonds, which generate two S(6) ring motifs. The central perylene core of 1 is twisted with dihedral angles of 19.48(2) • and 19.50(2) • ; this twist configuration induces the axial chirality in this family of perylene bisimide chromophores. Density functional theory (DFT) calculations also show that the core twist angles of 1,6-diaminoperylene bisimide are larger than those of 1,7-diaminoperylene bisimide, which may account for the fact that the 1,7-regioisomer has a more extended effective conjugation length than the 1,6-regioisomer.

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“…The absorption and photoluminescence (PL) peaks of the PDI with four fluorine atoms on the bay‐positions (1,6,7,12‐positions) have found to be blue‐shifted relative to those of the PDI with two fluorine atoms on the bay‐positions (1,7‐positions) . The PL spectra of the PDIs with electron‐donating groups on the bay‐positions are red‐shifted by comparison with the PDIs with electron‐withdrawing substitutes . In addition, PDIs can be ortho‐substituted (2,5,8 and 11‐positions) via copper catalyzed reactions, in which the lowest unoccupied molecular orbital (LUMO) levels can be efficiently adjusted by substituents .…”

Section: Introductionmentioning

confidence: 99%

The effect of imide substituents on the optical properties of perylene diimide derivatives

2018

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As one of the most important organic semiconductors, perylene diimide derivatives (PDIs) have been widely applied in optoelectronics. Two kinds of soluble PDIs with different imide substituents have been synthesized and their optical properties have been investigated. The photoluminescence (PL) intensity of the PDI with amino phenyl imide substituents (NH -PDI) is much lower than that of the PDI with octyl imide substituents (O-PDI). It can be found that the Stokes shift of O-PDI is positive, whereas, the Stokes shift of NH -PDI is negative. The emission intensity of the 0-0 electron transition relative to that of the 1-0 electron transition (I /I ) in the PL spectrum of O-PDI is decreased, but the value of I /I in the PL spectra of NH -PDI is increased as the dielectric constant of the solvent increases. The large overlap between the absorption and PL spectra plays an important role to result in the low PL intensity of NH -PDI. The PL decay data show that a non-radiative process, photoinduced electron transfer, also contributes to the low PL intensity of NH -PDI. The results can help researchers to understand the effect of the imide substituents on the optical properties of PDIs.

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1,6- and 1,7-Regioisomers of Asymmetric and Symmetric Perylene Bisimides: Synthesis, Characterization and Optical Properties

Abstract: The 1,6-and 1,

Cited by 20 publications

References 73 publications

Nitro-Perylenediimide: An Emerging Building Block for the Synthesis of Functional Organic Materials

Nitro-Perylenediimide: An Emerging Building Block for the Synthesis of Functional Organic Materials

1,6-Diaminoperylene bisimide with a highly twisted perylene core

The effect of imide substituents on the optical properties of perylene diimide derivatives

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