2024
DOI: 10.1002/ejoc.202301161
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Nucleophilic Addition of Bulky Aryl Substituents to Pentacene‐6,13‐quinone

Johannes Schöntag,
Markus Ströbele,
Hartmut Schubert
et al.

Abstract: We investigate the introduction of bulky aryl substituents of the biphenyl, terphenyl, and quaterphenyl type at the 6,13 and 5,7,12,14 positions of the pentacene scaffold by reaction of the corresponding quinones with lithium organic reagents. The 1,1’‐biphenyl‐2‐yl substituent could be installed at the 5,7,12,14‐positions and regioselectively either at 6,13 or at the 5,13 positions. The dissymmetric substitution motif results from concomitant 1,2 and rare 1,4‐addition to 6,13‐pentacenequinone. A one‐pot proto… Show more

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Cited by 2 publications
(4 citation statements)
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“…It can also have consequences for the chemical reactivity, for instance 4A and 5A may behave differently upon nucleophilic attack (1,2- vs. 1,4-addition). 28,29 We found that most of the photophysical and chiroptical properties of 4A and 5A are comparable and only the absorbance maxima of 5A (480 nm, double bond in para -position to the carbonyl) is red-shifted by 12 nm when compared to 4A (468 nm, double bond in ortho -position to the carbonyl). However, the geometry strongly affects the redox behavior, as evidenced by cyclic voltammetry (CV).…”
Section: Resultsmentioning
confidence: 74%
“…It can also have consequences for the chemical reactivity, for instance 4A and 5A may behave differently upon nucleophilic attack (1,2- vs. 1,4-addition). 28,29 We found that most of the photophysical and chiroptical properties of 4A and 5A are comparable and only the absorbance maxima of 5A (480 nm, double bond in para -position to the carbonyl) is red-shifted by 12 nm when compared to 4A (468 nm, double bond in ortho -position to the carbonyl). However, the geometry strongly affects the redox behavior, as evidenced by cyclic voltammetry (CV).…”
Section: Resultsmentioning
confidence: 74%
“…Diagonal Crisscross Bridging of Pentacenes. Opposing biphenyl substituents face different hemispheres in Pen3, 134,135 a consequence of steric demand and the electrostatic repulsion between alkoxide and organometallic species during synthesis�their orientation predisposes them toward ring closure across the pentacene backbone. The resulting cyclophenylene halves helically wrap the pentacene chromophore on both sides�to describe this topology resembling the bannister of spiral staircase revolving around a central pillar, Vogtle introduced the term "Gelander" (engl.…”
Section: Increasing Steric Hindrance: σ-Dimersmentioning
confidence: 99%
“…Acenes were clipped into macrocycles to improve their light fastness and some of their open congeners. R = 3,5-di- tert -butylphenyl. , …”
Section: Alternative Ways To Improve the Persistence Of (Aza-)acenesmentioning
confidence: 99%
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