Control of the molecular packing of chloroboron(iii) and fluoroboron(iii) subnaphthalocyanines by designing peripheral substituents

Abstract

Dipolar subnaphthalocyanines with alkynyl groups and a B–F moiety are packed in hexagonal columns.

Phenoxy-(Chloro)n-Boron Subnaphthalocyanines: Alloyed Mixture, Electron-Accepting Functionality, and Enhanced Solubility for Bulk Heterojunction Organic Photovoltaics

“…Additionally, Takagi and Mizutani were able to characterize the bay position resonances in a recent study due to the lack of bay position chlorination. 36 However, unlike these findings, the multiplicity of the bay position hydrogens for PhO-Cl n BsubNc and F 5 -Cl n BsubNc was found to be multiplets as opposed to singlets. The multiplet patterns are caused by the presence of the asymmetric randomly bay-chlorinated BsubNc isomers, as opposed to a single compound.…”

“…In the study of Takao and Ohno, all peripheral positions other than the bay position of the BsubNc structure were fluorinated, allowing for the 1 H NMR characterization of the bay position hydrogens. Additionally, Takagi and Mizutani were able to characterize the bay position resonances in a recent study due to the lack of bay position chlorination . However, unlike these findings, the multiplicity of the bay position hydrogens for PhO-Cl n BsubNc and F 5 -Cl n BsubNc was found to be multiplets as opposed to singlets.…”

Recent advances in subphthalocyanines and related subporphyrinoids

“…562 Moreover, substitution by fluoride is carried out by treatment with AgBF 4 in toluene. 449,561,563–565…”

“…562 Moreover, substitution by fluoride is carried out by treatment with AgBF 4 in toluene. 449,561,[563][564][565] 1,2-Subnaphthalocyanines were prepared for the first time by Kobayashi and Nyokong by cyclotrimerization reaction of 1,2-naphthalenedicarbonitrile under standard conditions, giving rise to a 1 : 3-1 : 6 mixture of the C 3 and C 1 regioisomers of 342, which were identify by X-ray diffraction analysis. The four stereoisomers (Scheme 31) could be separated by column chromatography, followed by chiral HPLC.…”

Exploring the Effects of Bay Position Chlorination on the Emissive Properties of Chloro-(Chloro)n-Boron Subnaphthalocyanines for Light Emission.

“…Boron subnaphthalocyanines (BsubNcs, Figure 1) are a subgroup of the phthalocyanine macrocyclic family, which have attracted interest as functional organic semiconductors [1][2][3][4] and sensor materials [5] because of their synthetic tunability [6][7][8][9] and high thermal, chemical and photo-stability. [10][11][12] Structurally BsubNcs, and their counterparts boron subphthalocyanine (BsubPc), [13] differ from conventional metal-and metalloid-phthalocyanines (MPcs) [14] because of their molecular non-planar conformation and reduced trimeric ligand structure.…”