2011
DOI: 10.1021/jo2001963
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Abstract: Perylene-3,4,9,10-tetracarboxylic acid diimides (perylene diimides, PDIs) have been used as industrial pigments for many years. More recently, new applications for PDI derivatives have emerged in areas including organic photovoltaic devices and field-effect transistors. This Perspective discusses the synthesis and physical properties of PDI derivatives and their applications in organic electronics.

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Cited by 966 publications
(864 citation statements)
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“…Pichierri [9] also observed that E H-L remains almost constant for N-alkyl and N-aryl derivatives of PDI, due to a strong linear correlation (R 2 = 0.9994) between E LUMO and E HOMO . As Huang et al [31] have noted, the nitrogen atoms of PDI are at a nodal plane for both the HOMO and LUMO. Therefore, the introduction of substituents at N is likely to have only an inductive effect on both frontier orbitals, leading to little change in E H-L and the optical properties.…”
Section: A C C E P T E D Accepted Manuscriptmentioning
confidence: 91%
“…Pichierri [9] also observed that E H-L remains almost constant for N-alkyl and N-aryl derivatives of PDI, due to a strong linear correlation (R 2 = 0.9994) between E LUMO and E HOMO . As Huang et al [31] have noted, the nitrogen atoms of PDI are at a nodal plane for both the HOMO and LUMO. Therefore, the introduction of substituents at N is likely to have only an inductive effect on both frontier orbitals, leading to little change in E H-L and the optical properties.…”
Section: A C C E P T E D Accepted Manuscriptmentioning
confidence: 91%
“…N‐substitution of PDIs can also influence their self‐assembly properties, which has stimulated intensive studies into bulk and solution‐based applications of these compounds 29, 30, 31, 32. By contrast, substitution of the perylene ring system at either the ortho ‐ or bay positions can significantly influence the optical and solubility properties of the PDIs, dependent upon the substitution pattern, the steric bulk and electronic properties of the substituent group 33, 34, 35, 36. Bay substitution, for example, increases steric hindrance in this region of the molecule, which is relieved by out‐of‐plane twisting of the PDIs perylene ring system.…”
Section: Introductionmentioning
confidence: 99%
“…This phenomenon causes a disruption to the π–π stacking behaviour of the PDI, which leads to improved solubility and altered physical properties 33, 37. Substitution of PDIs at the bay position is, however, synthetically demanding, involves halogenation reactions, and predominantly four‐fold bay‐substituted PDIs have been reported 35, 38, 39, 40, 41, 42, 43. Partly substituted 1,6‐ and 1,7‐regioisomers, commonly as mixtures,44, 45, 46, 47, 48 have also been synthesised,49, 50 while 1,12‐bay‐substituted PDIs have been rarely reported.…”
Section: Introductionmentioning
confidence: 99%
“…Furthermore, PDI redox potentials can be tuned, most effectively through substitutions at the "bay" (1,6,7,12) and/or "ortho" (2,5,8,11) positions, allowing them to be energetically matched to different active-layer and TCO materials. 25,26 In a recent study, 27 we began examining the properties of PDI monolayers tethered to ITO via phosphonic acid (PA) anchoring groups. ET rate constants exceeding 10 3 s -1 were measured for PDI-PA monolayers on ITO, and a dependence on the bridge length, which dictated the tunneling distance, was demonstrated.…”
Section: Introductionmentioning
confidence: 99%