Library of Azabenz-Annulated
Core-Extended Perylene
Derivatives with Diverse Substitution Patterns and Tunable Electronic
and Optical Properties
Version 2 2016-09-12, 13:03
Version 1 2016-08-26, 21:17
Posted on 2016-08-29 - 00:00
Here,
we present a collection of different azabenz-annulated perylene
derivatives. By developing new synthetic strategies and improving
existing protocols, we have expanded the structural diversity of these
dye molecules to a multifunctional class of ligating chromophores.
The Pictet–Spengler (PS) reaction of 1-amino-perylenes with
different aldehydes is used to modify the terminal substitution pattern.
PS transformations of 1,6- and/or 1,7-diamino perylenes result in
2-fold annulated nitrogen-containing coronene-type molecules like anti-(ab)2-PBI 15, syn-(ab)2-PBI 16, and syn-(ab)2-PTE 18. In addition, azabenz-annulated perylene
bisanhydrides (ab-PBA 6 and syn-(ab)2-PBA 19) were explored as universal starting
materials providing access to any desired imide functionality. Furthermore,
a newly developed regioselective nitration procedure for perylene
monoimide diesters (PMIDE) enables the synthesis of 1-nitro-PMIDE 10 and thus of azabenz-annulated perylene derivatives with
unsymmetric peri-substitution patterns (ab-PMIDE 12 and ab-PMIMA 13). According to our spectroscopic
and theoretical investigations, the optical and electrochemical properties
of these multifunctional chromophores can easily be modified and adjusted
to many desirable applications following the synthetic strategies
presented in this work.
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Schulze, Marcus; Philipp, Michael; Waigel, Waldemar; Schmidt, David; Würthner, Frank (2016). Library of Azabenz-Annulated
Core-Extended Perylene
Derivatives with Diverse Substitution Patterns and Tunable Electronic
and Optical Properties. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.6b01573
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AUTHORS (5)
MS
Marcus Schulze
MP
Michael Philipp
WW
Waldemar Waigel
DS
David Schmidt
FW
Frank Würthner
KEYWORDS
multifunctional classTunable Electronicelectrochemical properties1- amino-perylenesligating chromophoresdye moleculesimide functionalityPBA 191- nitro-PMIDE 10ab-PMIDE 12Diverse Substitution Patternsab-PBA 6PBI 15PBI 16strategyAzabenz-Annulated Core-Extended Perylene Derivativesazabenz-annulated perylene derivativesmultifunctional chromophoresperylene monoimide diestersunsymmetric periterminal substitution patternPTE 18substitution patternsPS transformationsOptical Propertiessynannulated nitrogen-containing coronene-type moleculesab-PMIMA 13azabenz-annulated perylene bisanhydridesregioselective nitration procedure