Synthesis of a soluble fulleropyrrolidine derivative for use as an electron acceptor in bulk-heterojunction polymer solar cells

Mi, Dongbo; Kim, Hee-Un; Kim, Ji‐Hoon; Xu, F.; Jin, Sung‐Ho; Hwang, Do‐Hoon

doi:10.1016/j.synthmet.2012.01.004

Cited by 21 publications

(9 citation statements)

References 32 publications

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“…Under the premise that the energy level of ferrocene/ferrocenium is 4.8 eV below the vacuum level, [14] the highest-occupied molecular orbital (HOMO) energy levels of 1-3 can be estimated according to: E HOMO = À[E onset ox1 + 4.8] (eV), where E onset ox1 is the onset oxidation potential of the first redox wave versus Fc/Fc + . [15] For the three molecules, the HOMO levels were found in the range À4.5 to À4.8 eV. No reduction processes were observed under the used conditions for any of the molecules down to À1.5 V vs. Ag(s).…”

Section: Electrochemistrymentioning

confidence: 84%

HOMO Stabilisation in π‐Extended Dibenzotetrathiafulvalene Derivatives for Their Application in Organic Field‐Effect Transistors

Geng

Pfattner

Campos

et al. 2014

Chemistry A European J

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Three new organic semiconductors, in which either two methoxy units are directly linked to a dibenzotetrathiafulvalene (DB-TTF) central core and a 2,1,3-chalcogendiazole is fused on the one side, or four methoxy groups are linked to the DB-TTF, have been synthesised as active materials for organic field-effect transistors (OFETs). Their electrochemical behaviour, electronic absorption and fluorescence emission as well as photoinduced intramolecular charge transfer were studied. The electron-withdrawing 2,1,3-chalcogendiazole unit significantly affects the electronic properties of these semiconductors, lowering both the HOMO and LUMO energy levels and hence increasing the stability of the semiconducting material. The solution-processed single-crystal transistors exhibit high performance with a hole mobility up to 0.04 cm(2) V(-1) s(-1) as well as good ambient stability.

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Section: Electrochemistrymentioning

confidence: 84%

HOMO Stabilisation in π‐Extended Dibenzotetrathiafulvalene Derivatives for Their Application in Organic Field‐Effect Transistors

Geng

Pfattner

Campos

et al. 2014

Chemistry A European J

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“…30 Consequently, donor−acceptor dyads comprised of phenothiazine and fulleropyrrolidine (PTZ-C 60 ) have been investigated for their ability to undergo photochemical charge separation 31−33 and applications in organic solar cells. 34,35 It has been suggested that the donor−acceptor dyads provide sufficient HOMO− HOMO and LUMO−LUMO offsets of the donor and acceptor entities to help exceed the Coulombic attraction of the hole− electron pair, which is necessary to overcome the exciton binding energy to avoid the back charge transfer. 34,35 In the present investigation, we have synthesized a new series of PTZ-C 60 dyads wherein the phenothiazine C-3 position (dyads 1 and 2) or the heteroatom N position (dyad 3) has been functionalized to possess fullerene (see Figure 1 for structures).…”

Section: Introductionmentioning

confidence: 99%

“…34,35 It has been suggested that the donor−acceptor dyads provide sufficient HOMO− HOMO and LUMO−LUMO offsets of the donor and acceptor entities to help exceed the Coulombic attraction of the hole− electron pair, which is necessary to overcome the exciton binding energy to avoid the back charge transfer. 34,35 In the present investigation, we have synthesized a new series of PTZ-C 60 dyads wherein the phenothiazine C-3 position (dyads 1 and 2) or the heteroatom N position (dyad 3) has been functionalized to possess fullerene (see Figure 1 for structures). In addition, dyads 1 and 2 are substituted with Nhexyl or tri(ethylene glycol) chains, respectively, for better solubility and miscibility needed in device fabrication.…”

Section: Introductionmentioning

confidence: 99%

“…Incidentally, phenothiazine (PTZ), which is an electroactive heterocyclic compound with electron-rich S and N atoms, have recently attracted considerable interest as electron donors and sensitizers in dye-sensitized solar cells (DSSCs) . Consequently, donor–acceptor dyads comprised of phenothiazine and fulleropyrrolidine (PTZ-C 60 ) have been investigated for their ability to undergo photochemical charge separation − and applications in organic solar cells. , It has been suggested that the donor–acceptor dyads provide sufficient HOMO–HOMO and LUMO–LUMO offsets of the donor and acceptor entities to help exceed the Coulombic attraction of the hole–electron pair, which is necessary to overcome the exciton binding energy to avoid the back charge transfer. , …”

Section: Introductionmentioning

confidence: 99%

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Syntheses, Charge Separation, and Inverted Bulk Heterojunction Solar Cell Application of Phenothiazine–Fullerene Dyads

Blanco

Hiltunen

Lim

et al. 2016

ACS Appl. Mater. Interfaces

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A series of phenothiazine-fulleropyrrolidine (PTZ-C60) dyads having fullerene either at the C-3 aromatic ring position or at the N-position of phenothiazine macrocycle were newly synthesized and characterized. Photoinduced electron transfer leading to PTZ(•+)-C60(•-) charge-separated species was established from studies involving femtosecond transient absorption spectroscopy. Because of the close proximity of the donor and acceptor entities, the C-3 ring substituted PTZ-C60 dyads revealed faster charge separation and charge recombination processes than that observed in the dyad functionalized through the N-position. Next, inverted organic bulk heterojunction (BHJ) solar cells were constructed using the dyads in place of traditionally used [6,6]-phenyl-C61- butyric acid methyl ester (PCBM) and an additional electron donor material poly(3-hexylthiophene) (P3HT). The performance of the C-3 ring substituted PTZ-C60 dyad having a polyethylene glycol substituent produced a power conversion efficiency of 3.5% under inverted bulk heterojunction (BHJ) configuration. This was attributed to optimal BHJ morphology between the polymer and the dyad, which was further promoted by the efficient intramolecular charge separation and relatively slow charge recombination promoted by the dyad within the BHJ structure. The present finding demonstrate PTZ-C60 dyads as being good prospective materials for building organic photovoltaic devices.

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“…Organic photovoltaic (OPV) cells are a promising solar energy harvesting technology because of their flexibility, light weight, and compatibility with large-scale production using roll-to-roll methods synthesized and tested by Mi et al [40] in P3HT-based devices with standard geometry. However, the devices achieved the best modest efficiency of only 1.42%.…”

Section: Introductionmentioning

confidence: 99%

Thiophene- and Carbazole-Substituted N-Methyl-Fulleropyrrolidine Acceptors in PffBT4T-2OD Based Solar Cells

et al. 2020

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The impact of fullerene side chain functionalization with thiophene and carbazole groups on the device properties of bulk-heterojunction polymer:fullerene solar cells is discussed through a systematic investigation of material blends consisting of the conjugated polymer poly[(5,6-difluoro-2,1,3-benzothiadiazol-4,7-diyl)-alt-(3,3‴-di(2-octyldodecyl)-2,2′;5′,2″;5″,2‴-quaterthiophen-5,5‴-diyl)] (PffBT4T-2OD) as donor and C60 or C70 fulleropyrrolidines as acceptors. The photovoltaic performance clearly depended on the molecular structure of the fulleropyrrolidine substituents although no direct correlation with the surface morphology of the photoactive layer, as determined by atomic force microscopy, could be established. Although some fulleropyrrolidines possess favorable lowest unoccupied molecular orbital levels, when compared to the standard PC71BM, they originated OPV cells with inferior efficiencies than PC71BM-based reference cells. Fulleropyrrolidines based on C60 produced, in general, better devices than those based on C70, and we attribute this observation to the detrimental effect of the structural and energetic disorder that is present in the regioisomer mixtures of C70-based fullerenes, but absent in the C60-based fullerenes. These results provide new additional knowledge on the effect of the fullerene functionalization on the efficiency of organic solar cells.

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Synthesis of a soluble fulleropyrrolidine derivative for use as an electron acceptor in bulk-heterojunction polymer solar cells

Cited by 21 publications

References 32 publications

HOMO Stabilisation in π‐Extended Dibenzotetrathiafulvalene Derivatives for Their Application in Organic Field‐Effect Transistors

HOMO Stabilisation in π‐Extended Dibenzotetrathiafulvalene Derivatives for Their Application in Organic Field‐Effect Transistors

Syntheses, Charge Separation, and Inverted Bulk Heterojunction Solar Cell Application of Phenothiazine–Fullerene Dyads

Thiophene- and Carbazole-Substituted N-Methyl-Fulleropyrrolidine Acceptors in PffBT4T-2OD Based Solar Cells

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