Facile synthesis of 1-bromo-7-alkoxyl perylene diimide dyes: toward unsymmetrical functionalizations at the 1,7-positions

A Potential Perylene Diimide Dimer‐Based Acceptor Material for Highly Efficient Solution‐Processed Non‐Fullerene Organic Solar Cells with 4.03% Efficiency

“…Synthesis of Bis‐PDI‐T‐EG : Bis‐PDI‐T‐EG was synthesized as follows (Scheme S1, Supporting Information). The 1‐(2‐methoxyethoxyl)‐7‐brominated perylene diimide 2 was synthesized following our reported procedure . A mixture of 2 (168.6 mg, 0.22 mmol) and 2,5‐bis(tributylstannyl) thiophene ( 3 , 97%, 0.1 mmol) was dissolved in dry toluene (10 mL).…”

“…Bis‐PDI‐T‐EG was synthesized by Stille coupling of 1‐EG‐7‐brominated PDI ( 2 ) and 2,5‐bis(tributylstannyl) thiophene ( 3 ) . The final product was fully characterized with 1 H NMR, 13 C NMR, time‐of‐flight mass spectrometry (TOF‐MS), and elemental analysis (Experimental Section).…”

Concentration-dependent self-assembly structures of an amphiphilic perylene diimide with tri(ethylene glycol) substituents at bay positions

“…The synthetic scheme of 1,7-TEG-PDI-C 12 is shown in Scheme 1. Although 1,7-disubstituted amphiphilic PDI derivatives have been reported in several works, 15,[20][21][22][23] adding bifunctional substituent, such as TEG, onto 1,7-dibrominated PDI remains unexplored. Because both 1,7-dibrominated PDI and TEG are bifunctional, if the reaction conditions are not optimized, oligo(PDI)s or even poly(PDI) may be generated in the reaction, resulting in the low yield of 1,7-TEG-PDI-C 12 .…”

Synthesis and characterization of novel perylene dyes with new substituents at terminal-position as colorants for LCD color filter

“…The introduction of substituents in the bay position also increases steric restriction within dye structures [5], and the planarity of dyes will be decreased [11]. However, the substituents in the bay position were attached to the main body via an ether linkage, so that the substituents had significant influence on the spectral properties of the dyes [12].…”