New Donor–Acceptor Materials Based on Random Polynorbornenes Bearing Pendant Phthalocyanine and Fullerene Units

Abstract

New donor-acceptor materials based on a polynorbornene framework to which both phthalocyanine and C60 electroactive pendant units are randomly attached have been prepared in good yield by ring-opening-metathesis polymerization (ROMP) in the presence of a Grubbs catalyst. A structurally related phthalocyanine homopolymer was also synthesized for comparison. A remarkable fluorescence quenching was observed in the homopolymer and accounts for PcPc interactions along the polymeric framework. As expected, the fluorescence quenching increases in the case of the polynorbornenes containing both Pc and C60 units owing to photoinduced electron transfer, which was further confirmed by transient absorption spectroscopy. Finally, preliminary solar cell devices made of one of the copolymers were constructed.

Dye-functionalized polymers via ring opening metathesis polymerization: principal routes and applications

“…A wide range of suitable monomers has been copolymerized comprising (hetero)polyaromatic compounds [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33], and more sophisticated functionalities like conjugated oligomers [34][35][36][37][38][39], triphenylmethane [40][41][42][43][44][45][46][47], azo [48][49][50][51][52], or polymethine [53][54][55][56][57] dyes. Even transition metal coordination compounds of aluminum [58,59], iron [60], zinc [61][62][63], ruthenium [64, 65], europium …”

“…Fluorescence quenching in this copolymer was enhanced compared to blend systems with a phthalocyanine-containing homopolymer. Although these copolymers can harvest photons with wavelengths up to the infrared region and the fluorescence spectra of the copolymers indicated a strong excitonic coupling, only moderate conversion efficiencies could be achieved so far [61]. Another approach for the preparation of PV cells was carried out by Marder et al where perylene-3,4,9,10-tetracarboxylic diimides have been linked to a norbornene moiety.…”

“…Using the different approaches outlined above, precise placement of the dyes in either the hydrophilic or the hydrophobic block as well as on either chain is possible while the ratio of hydrophilic and hydrophobic blocks can be adjusted simply by employing adequate monomer/initiator Fig. 8 Zn-porphyrine/fullerene random copolymer [61] and perylenebisimide monomers for the preparation of PV cells [23] Fig. 9 Electrochromic ROMP monomer (20) and optical images and UV-Vis spectra of the resulting polymer.…”

Efficient Sensitization of Nanocrystalline TiO2 Films by a Near‐IR‐Absorbing Unsymmetrical Zinc Phthalocyanine

“…Phthalocyanines (Pc) are well known for their intense absorption in the red/near-IR (Q band) regions, therefore they are an excellent alternative for solar-cell applications. [14][15][16][17] As well as providing good absorption in the red/near-IR region of the solar spectrum, phthalocyanines can be tuned to be transparent over a large region of the visible spectrum, thereby enabling the possibility of using them as "photovoltaic windows": a red/near-IR absorbing photovoltaic cell, in place of a window, will allow visible light to enter a building whilst harvesting the solar power from the red/near-IR part of the spectrum. In addition to directly generating power, this also reduces the solar heating of buildings, thereby reducing the demand for, and power consumption of, airconditioning units.…”

Hydrogen‐Bonding‐Induced One‐Handed Helical Polynorbornenes Appended With Chiral Alaninegland

“…[ 1 ] Incorporation of amino acid or peptide residues onto polyisocyanides [ 2 ] and poly(phenylacetylene) s [ 3 ] are known to induce one-handed helicity of polymers. Polynorbornenes (PNBs) obtained by metal-catalyzed ring opening metathesis polymerization (ROMP) of the corresponding norbornene derivatives [ 4 ] are useful for catalysis, [ 5 ] light harvesting and photoinduced electron transfer, [ 6 ] ion conductivity, [ 7 ] and optoelectronic applications. [8][9][10][11][12] Although chiral catalysts have been used for the synthesis of PNBs, [ 13 ] incorporation of chiral auxiliary into…”