Anion–π interactions of highly π-acidic dipyridinium-naphthalene diimide salts

Abstract

A highly π-acidic dipyridinium-naphthalene diimide acceptor shows anion-π interactions with halides and PF6-. Lewis basicity and redox potential of the anion affect the chemistry, and photophysical and electrochemical properties, as well as both ionic and electrical conductivities. Our results provide insights into doping, degradation and ion transport mechanisms in organic n-type semiconductors.

Thermoelectric Performances of n-Doped Ladder-Type Conjugated Polymers Using Various Viologen Radical Cations

“…The peak positions for the λ max are 732 nm for HV·I, 731 nm for HV·Cl, 730 nm for BV·I, and 728 nm for BV·Cl. Such trends in UV–vis absorption have also been observed in other organic (radical) salts. , The peak position of the first reduction of the viologens (V 2+ → V 1+ ) in the cyclic voltammogram also showed a subtle difference, with increasing negative reduction potential in the order BV·2Cl (−1.29 V) > BV·2I (−1.31 V) > HV·2Cl (−1.38 V) > HV·2I (−1.41 V). We note that the trend in the first reduction potential is the same as the λ max .…”

“…Such trends in UV−vis absorption have also been observed in other organic (radical) salts. 33,34 The peak position of the first reduction of the viologens (V 2+ → V 1+ ) in the cyclic voltammogram also showed a subtle difference, with increasing negative reduction potential in the order BV…”

Targeted Synthesis of NIR Luminescent Rhenium Diimine cis,trans‐[Re()(CO)2(L)2]n+ Complexes Containing N‐Donor Axial Ligands: Photophysical, Electrochemical, and Theoretical Studies

“…The distortions are dictated by crystal packing, which is determined by intermolecular π-π interactions ( (3.63 Å) between the N-methylated pyridine fragment and iodide anion are presented in the crystal cell similar to previously published analogous structures. [49][50][51][52] Short contacts C•••O (3.15 Å) are also found between the N-methylated pyridine fragment and water molecule; this type of interaction could be described in terms of lone-pair -π-system interaction. [52,53] occur in electron deficient π-systems.…”

Azine Steric Hindrances Switch Halogen Bonding to N‐Arylation upon Interplay with σ‐Hole Donating Haloarenenitriles

“…[61][62][63] Only a few cases of conventional S N Ar reactions, where EWG groups activate the Xbound ipso-carbon toward the nucleophilic attack have been reported. These reactions include 2,4-dinitrobromobenzene, [64,65] 2,4-dinitroiodobenzene, [66] 2,4,6-trinitroiodobenzene, [67] tetrabromocatechol, [68][69][70] bromopyromellitic diimide, [71] and 2,3dibromonaphthalene-1,4,5,8-tetracarboxylic acid bisimide [72,73] as the arylation agents. All these reactions were conducted at high to moderate temperatures depending on the activating effect of substituents.…”