Progress in the synthesis of perylene bisimide dyes

Nowak‐Król, Agnieszka; Würthner, Frank

doi:10.1039/c8qo01368c

Cited by 271 publications

(296 citation statements)

References 217 publications

Supporting

Mentioning

279

Contrasting

Order By: Relevance

“…Solvents were dried according to standard procedures. The 1 H-, 13 [64] The MALDI mass spectra were obtained from aB ruker apex-Qe FT-ICR spectrometer and aB ruker Autoflex Speed MALDI-TOFs pectrometer.T he absorption spectra were recorded on aC ary 500 UV/Vis/NIR spectrophotometer and were baseline and solvent corrected. Emission spectra were measured on aV arian Cary Eclipse Spectrophotometer.D escription how Fluorescence quantum yields were obtained is explained in detail in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

“…Perylene tetracarboxydiimides (PDIs) have been extensively studied as functional dyes and electronic materials. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] Their properties may be variedw idely by substitution at the perylene core and at the imido-N position. The carboxys ubstituents at the central perylene core rendert hese materials electron acceptors, and this propertyi np articularh as been underlying their application in organic electronics.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Twisting the TAPPs: Bay‐Substituted Non‐planar Tetraazapero‐pyrenes and their Reduced Anions

Günther

Höfener

Zschieschang

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

A new synthesis of tetraazaperopyrenes (TAPPs) starting from a halogenated perylene derivative 3,4,9,10‐ tetrabromo‐1,6,7,12‐tetrachloroperylene (1) gave access to bay‐substituted TAPPs for the first time. Selective lithiation of the bromine‐positions and subsequent addition of tosyl azide led to the formation of the tetraazidotetrachloroperylene (2), which was subsequently reduced by addition of sodium borohydride to the corresponding tetraaminotetrachloroperylene (3). Oxidation to its semiquinoidal form 4 and subsequent cyclization with acid chlorides gave rise to a series of bay‐chlorinated TAPPs. Whereas the aromatic core of the previously studied ortho‐substituted TAPPs was found to be planar, the steric pressure of the two chlorine substituents on each side leads to the twist of the peropyrene core of approximately 30 degrees, a structural feature also observed in other bay‐substituted perylene derivatives. An experimental and computational analysis reveals that introducing chloride substituents at these positions leads to slightly increased electron affinities (EA) enabling the selective generation and characterization of the reduced mono‐anionic radicals and closed shell di‐anionic species. These anions were isolated and characterized by UV/Vis spectroscopy and EPR or NMR, respectively. Processing of the bay‐chlorinated TAPPs in n‐channel organic TFTs revealed electron mobilities of 0.001 to 0.003 cm2 V−1 s−1. These reduced electron mobilities compared to the ortho‐halogenated TAPPs are thought to be rooted in the less densely packed solid‐state structures.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Twisting the TAPPs: Bay‐Substituted Non‐planar Tetraazapero‐pyrenes and their Reduced Anions

Günther

Höfener

Zschieschang

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…For the mono and bis bromination reactions, numerous synthetic strategies have been reported [29]. Nevertheless, the most used pathway using the milder conditions is shown in Scheme 1.…”

Section: Nitration Vs Bromination Conditions Of Perylenediimide Derimentioning

confidence: 99%

“…All those strategies have been widely applied to PDI derivatives, mostly through the functionalization of the perylene core at the ortho or bay positions, as modifications at the imide position barely influence the photoredox properties but mostly affect the solubility of the material. [28,29] Historically, the functionalization of the perylene core has been achieved via the formation of key halogenated-PDIs intermediates in the positions 1,12 and 6,7 (bay region); in particular, 1,6,7,12-tetrachlorinated or 1-mono and 1,6/1,7-dibrominated PDIs. In this review, we will present the emergence of nitro-substituted PDIs as new key intermediates for modifying the molecular structure of the PDI core and efficiently tuning its HOMO-LUMO band gap (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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

2020

View full text Add to dashboard Cite

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.

show abstract

“…Apart from the A-D-A-type NFAs, perylene diimide (PDI) units have also come into wide use for constructing n-type organic semiconductors. [49][50][51][52][53][54] Indeed, PDI derivatives are the earliest and most common NFAs, which generally exhibit strong electron-accepting capability, strong absorption, high electron mobility on par with those of FAs, and excellent thermal and oxidative stability. [55][56][57] Despite the aforementioned strengths, PDI acceptors tend to form large aggregates due to their large planar structures, which presumably bring out severe geminate recombination and excessive domain sizes, thus leading to detrimental effects to device performances.…”

Section: Introductionmentioning

confidence: 99%

Chalcogen‐Fused Perylene Diimides‐Based Nonfullerene Acceptors for High‐Performance Organic Solar Cells: Insight into the Effect of O, S, and Se

Wang

et al. 2019

Solar RRL

View full text Add to dashboard Cite

Three perylene diimide (PDI) tetramers annulated by oxygen (O), sulfur (S), and selenium (Se), named as SF‐4PDI‐O, SF‐4PDI‐S, and SF‐4PDI‐Se, are designed, synthesized, and paired with polymeric donor PDBT‐T1 to construct organic solar cells. The heteroatoms' effects on photoelectric properties, chemical geometry, charge transport, active‐layer morphology, and photovoltaic performance are investigated in detail. These PDI acceptors exhibit a similar absorption profile, whereas the highest occupied molecular orbitals and lowest unoccupied molecular orbitals are simultaneously upshifted when heteroatoms are altered from O and S to Se due to the gradually weakening electronegativity. Alongside PDBT‐T1, SF‐4PDI‐O achieves an outstanding power conversion efficiency of 8.904% with a high fill factor of 0.706, outcompeting its S‐annulated and Se‐annulated counterparts. The superiority of the PDBT‐T1:SF‐4PDI‐O system lies in its stronger crystallinity, more balanced hole and electron mobilities, and weaker bimolecular recombination, coupled with more efficient charge transfer and collection. These results shed light on the invention of high‐performance PDI acceptors by oxygen‐decorated methodology.

show abstract

Progress in the synthesis of perylene bisimide dyes

Abstract: Rapid progress in the synthesis of perylene bisimide dyes gave an old scaffold new life.

Cited by 271 publications

References 217 publications

Twisting the TAPPs: Bay‐Substituted Non‐planar Tetraazapero‐pyrenes and their Reduced Anions

Twisting the TAPPs: Bay‐Substituted Non‐planar Tetraazapero‐pyrenes and their Reduced Anions

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

Chalcogen‐Fused Perylene Diimides‐Based Nonfullerene Acceptors for High‐Performance Organic Solar Cells: Insight into the Effect of O, S, and Se

Contact Info

Product

Resources

About