Syntheses and Properties of 1,6 and 1,7 Perylene Diimides and Tetracarboxylic Dianhydrides

Handa, Nisha V.; Mendoza, Kayla D; Shirtcliff, Laura D.

doi:10.1021/ol2019407

Cited by 53 publications

(27 citation statements)

References 45 publications

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“…The electronic characteristics of PBIs can also be fine-tuned by the substitution of the conjugated aromatic core. Based on these principles, many perylene bisimide derivatives with either electron-withdrawing or electron-donating groups have been reported in the literature, including: (1) cyano-substituted PBIs [56,57]; (2) nitro-substituted PBIs [58,59,60]; (3) perfluoroalkyl-substituted PBIs [61,62]; (4) aryl-substituted PBIs [63,64]; (5) ferrocenyl-substituted PBIs [65,66]; (6) boryl-substituted PBIs [67]; (7) alkyl-substituted PBIs [68]; (8) hydroxy-substituted PBIs [69,70]; (9) alkoxy-substituted PBIs [71,72,73,74,75]; (10) amino-substituted PBIs [76,77]; (11) alkylamino-substituted PBIs [78,79,80]; (12) pyrrolidinyl-substituted PBIs [81,82,83]; (13) piperidinyl-substituted PBIs [84,85,86]; etc .…”

Section: Introductionmentioning

confidence: 99%

Green Perylene Bisimide Dyes: Synthesis, Photophysical and Electrochemical Properties

Chang¹,

Tsai²,

Chen³

2014

Materials

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Three asymmetric amino-substituted perylene bisimide dyes with different n-alkyl chain lengths (n = 6, 12, or 18), 1-(N,N-dialkylamino)perylene bisimides (1a-1c), were synthesized under mild condition in high yields and were characterized by 1 H NMR, 13C NMR (nuclear magnetic resonance), HRMS (High Resolution Mass Spectrometer), UV-Vis and fluorescence spectra, as well as cyclic voltammetry (CV). These molecules show intense green color in both solution and solid state and are highly soluble in dichloromethane and even in nonpolar solvents, such as hexane. The shapes of the absorption spectra of 1a-1c in solid state and in solution were found to be virtually the same, indicating that the long alkyl chains could efficiently prevent aggregation. They exhibit a unique charge transfer emission in the near-infrared region, of which the peak wavelengths show strong solvatochromism. The dipole moments of the compounds have been estimated using the Lippert-Mataga equation, and upon excitation, they show larger dipole moment changes than that of 1-aminoperylene bisimide (2). Furthermore, all of the compounds exhibit two quasi-reversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory (DFT) calculations performed on these dyes are reported in order to rationalize their molecular structures and electronic properties.

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Section: Introductionmentioning

confidence: 99%

Green Perylene Bisimide Dyes: Synthesis, Photophysical and Electrochemical Properties

Chang¹,

Tsai²,

Chen³

2014

Materials

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“…The soluble symmetrically N,N'-substituted PDS are commonly obtained in the same way by using long chain alkyl groups. PDI molecules have insolubility problem in organic solvents [7].…”

Section: Introductionmentioning

confidence: 99%

“…Handa et al have synthesized 1,6 and 1,7 perylene diimides (PDIs) to obtain soluble molecule. It is possible to synthesis soluble perylene dimide via synthetic modification to N-alkyl or aryl PDIs and/or by modification of the "bay" region (1,6,7,12 positions) [7]. PDI derivatives substituted at the bay positions are obtained by using C-O, C-C and C-N coupling.…”

Section: Introductionmentioning

confidence: 99%

A Review on Perylene-3,4,9,10-Tetracarboxylic Acid Diimide Molecules

Birel¹

2017

Celal Bayar Üniversitesi Fen Bilimleri Dergisi

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The aim of this article is to inform about perylene-3,4,9,10-tetracarboxylic acid dimide (PDI) derivatives. Also, it is to give short and simple information about optical properties and using fields. Perylene-3,4,9,10-tetracarboxylic acid dimide derivatives known as perylene diimides are material of highly conjugated molecule. PDIs exhibit strong absorptions within the range of 400-450 nm (B band) and 500-700 nm (Q band). Perylene diimide dyes show generally characteristic absorption peaks at 458, 490, 526 nm. These absorption peaks are matched by the corresponding emission peaks at 540, 576, 624 nm, respectively. It has donor core and acceptor carbonyl groups. Perylene dimide has good electron mobility, high fluorescence quantum yields, strong absorption in the visible region, photostability, thermal stability, good semi-conductivity. These properties benefit them application of electronic material. Applications of PDIs are in the field of photo-electronic material, dye lasers, organic light-emitting diodes, and chemosensing materials.

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“…[29] In the literature, there are many derivatives of PBI such as (i) alkylsubstituted PBIs [28] ; (ii) pyrrolidinyl-substituted PBIs [30] ; (iii) nitro-substituted PBIs [31] ; (iv) ferrocenyl-substituted PBIs [32] ; (v) aryl-substituted PBIs [33] ; (vi) piperidinyl-substituted PBIs [34] ; (vii) alkoxy-substituted PBIs [35] ; (viii) cyano-substituted PBIs [36] ; and (ix) perfluoroalkyl-substituted PBIs. [37] Perylene derivatives such as PTCDIs have received considerable attention and are widely used as active compounds in various areas: in biochemical applications in telomerase inhibitors, [38] in pharmacological applications, [38] in fields of industrial, [39] in moleular electronic and optoelectronic devices [39] such as light-harvesting arrays, [39] molecular wires, [12] molecular switches, [39] optical switches, [40] liquid crystals, [41] transistors, [7,40] organic field-effect transistors, [42] and other electronic devices [43] because of their low-cost and commercial availability, [24] high electron accepting and transporting ability, [27] high molar absorption coefficient, [27,38] reversible redox properties, [44] unique optical and thermal properties, [38] electrochemical properties, [45] ease of their tunable absorption properties, [46] significant charge transport properties, [47] and ease of synthetic modification.…”

Section: Introductionmentioning

confidence: 99%

Investigation of the spectral, optical and surface morphology properties of theN,N′-Dipentyl-3,4,9,10-perylenedicarboximide small molecule for optoelectronic applications

Gündüz

2015

Polym. Adv. Technol.

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Investigation of the spectral, optical and surface morphology properties of the N,N′-Dipentyl-3,4,9,10-perylenedicarboximide small molecule for optoelectronic applications † Bayram Gündüz* The spectral and optical properties of the solutions of the N,N′-Dipentyl-3,4,9,10-perylenedicarboximide (PTCDI-C5) small molecule for different molarities were investigated in detail. The significant spectral parameters such as molar/mass extinction coefficients, absorption coefficient, electric dipole line strength, and oscillator strength of the PTCDI-C5 molecule were calculated. The absorption bands of PTCDI-C5 show vibronic structures with seven peaks at 2.08, 2.35, 2.53, 2.70, 2.86, 3.32, and 3.86 eV, respectively. The electronic spectra of the PTCDI-C5 can be characterized by two basic regions as visible and Soret band. Effects of the molarities on the significant many optical parameters were investigated in detail. The direct and indirect allowed optical band gaps of the PTCDI-C5 decrease with increasing molarity. Then, surface morphology properties were investigated and calculated roughness parameters of the PTCDI-C5 film. Finally, we discussed for optoelectronic applications of these parameters, and this study was compared with the similar and related studies in the literature.

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Syntheses and Properties of 1,6 and 1,7 Perylene Diimides and Tetracarboxylic Dianhydrides

Cited by 53 publications

References 45 publications

Green Perylene Bisimide Dyes: Synthesis, Photophysical and Electrochemical Properties

Green Perylene Bisimide Dyes: Synthesis, Photophysical and Electrochemical Properties

A Review on Perylene-3,4,9,10-Tetracarboxylic Acid Diimide Molecules

Investigation of the spectral, optical and surface morphology properties of theN,N′-Dipentyl-3,4,9,10-perylenedicarboximide small molecule for optoelectronic applications

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