New photoluminescent conjugated polymers with 1,4-dioxo-3,6-diphenylpyrrolo[3,4-c]pyrrole (DPP) and 1,4-phenylene units in the main chain

Red Emitting Diphenylpyrrolopyrrole (DPP)‐Based Polymers Prepared by Stille and Heck Coupling

“…[4] In order to use the DPP chromophore in electronic devices, it is therefore necessary to prepare soluble and film forming DPP compounds such as oligomers, [5] dendrimers, [6] and polymers. [7][8][9][10][11][12][13][14][15] These materials show intense red color, strong red photoluminescence, and electroluminescence, [12,14] which renders them attractive as active materials in a variety of electronic devices.…”

“…[11,12,14,15] Especially, the latter approach allows for the preparation of a variety of new DPP-containing p-conjugated polymers. Up to now, mainly Suzuki-type [16] arene-arene coupling reactions 2206 DOI: 10.1002/macp.200600363 Full Paper Summary: Six new soluble conjugated polymers are described, which were prepared by Stille and Heck polycondensation reactions.…”

“…[11,12,14,15] Only one example of Stille coupling [17] has been reported yet to yield a conjugated copolymer containing a few mole percent of DPP only. [7] DPP polymers prepared upon Heck coupling [18] were not reported so far.…”

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

“…159 Beyerlein and co-workers synthesised the luminescent and photostable p-conjugated polymer building blocks 108, 109a and 109b employing the SM cross-coupling reaction. 160 Similarly, Dehaen's group developed both convergent and divergent approaches for the synthesis of highly soluble rod-like diketopyrrolopyrrole oligomers of specified length by using the Pd(PPh 3 ) 4 -catalysed SM cross-coupling reaction of the diboronic ester 111 and the brominated 1,4-dioxo-3,6-diphenylpyrrolo [3,4-c]pyrroles (DPPs) 110a and 110b. An example of the convergent approach for the trimer of DPP 112 is included in Scheme 56.…”

Novel, soluble diphenyl-diketo-pyrrolopyrroles: Experimental and theoretical study

“…Furthermore, some of their physical properties such as high melting points are exceptional in view of their very low M r , in conventional pigment molecule terms. It has been shown that DPP units introduced into various materials, such as polymers [14][15][16][17][18][19][20][21][22][23] dendrimers [24], polymer-surfactant complexes [25], and oligomers [26] results in deeply coloured, highly photoluminescent [15][16][17][18][19][20][21][22][23][24][25][26] and electroluminescent [19,20] materials. Owing to their interesting properties, there is wide range of possible applications which have been already investigated covering for example latent pigment [27], charge generating materials for laser printers and information storage systems [28][29][30][31][32][33], solid-state dye lasers [30] or gas detectors [34,35].…”