Synthesis and characterisation of fluorenone–thiophene-based donor–acceptor oligomers: role of moiety sequence upon packing and electronic properties

Porzio, William; Destri, Silvia; Pasini, Mariacecilia; Giovanella, Umberto; Ragazzi, Massimo; Scavia, Guido; Kotowski, D.; Zotti, Gianni; Vercelli, Barbara

doi:10.1039/c0nj00045k

Cited by 34 publications

(12 citation statements)

References 47 publications

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“…The obtained results indicate that the HOMO is essentially localized at the HT units (and partially on the BT unit), which also explains similar HOMO levels for P4 and P5 (–5.53 eV). Similar observations relating to the impact of the positions of alkyl chains on thiophene rings on the optoelectronic properties of various copolymers based on alkylthiophenes and various acceptors including BT units have been reported in the literature 19,24. Because the open‐circuit voltages ( V oc values) of polymer solar cells shows linear correlation with the differences between the HOMO level of the electron donor and the LUMO level of the electron acceptor, the lower HOMO levels for some of the synthesized copolymers could result in higher V oc values for the corresponding polymer solar cells 12e…”

Section: Resultssupporting

confidence: 82%

Alternating Copolymers Based on 2,1,3‐Benzothiadiazole and Hexylthiophene: Positioning Effect of Hexyl Chains on the Photophysical and Electrochemical Properties

et al. 2011

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A series of donor–acceptor alternating π‐conjugated copolymers based on 2,1,3‐benzothiadiazole and hexylthiophene units has been synthesized by the palladium‐catalyzed Stille cross‐coupling method. Various precursory monomers possessing dibromo and bis(tributylstannyl) functionalities were readily prepared in high yields. Microwave‐assisted polymerization proved efficient for the production of high‐molecular‐weight copolymers, ranging from 13550 to 52490 g mol–1. All copolymers exhibited excellent solubilities in most common organic solvents. The thermal properties of these copolymers were investigated by thermogravimetric analysis and differential scanning calorimetry, and the polymers showed high thermal stabilities. Incorporation of the benzothiadiazole unit into polyhexylthiophene chains affected the photophysical and electrochemical properties. The thin‐film absorption spectra of all polymers are significantly red‐shifted relative to the corresponding absorption bands in solution and exhibit broader absorption bands. The optical band gaps were estimated to be in the range of 2.02–1.74 eV. The highest occupied and lowest unoccupied molecular orbital energy levels are in the ranges of –5.37 to –5.66 eV and –3.33 to –3.44 eV, respectively. In the X‐ray diffraction analysis of the deposited film of the copolymer P3, strong diffraction peaks were observed at 2θ = 5.72° (15.43 Å) and 23.12° (3.84 Å). These values relate to the distances between chains with interdigitated hexyl chains and to π–π stacking between the conjugated chains.

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Section: Resultssupporting

confidence: 82%

Alternating Copolymers Based on 2,1,3‐Benzothiadiazole and Hexylthiophene: Positioning Effect of Hexyl Chains on the Photophysical and Electrochemical Properties

et al. 2011

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“…prepared fluorenone end‐capped sexithiophene 69 and used it as donor material in BHJ solar cells. Devices prepared using 69 : 160 (1:1, w/w) reached maximum PCEs of about 0.8 % under AM 1.5, 100 mW cm −2 illumination 122…”

Section: Bulk‐heterojunction Solar Cells Made Of Small Molecules Bmentioning

confidence: 99%

Small Molecule Organic Semiconductors on the Move: Promises for Future Solar Energy Technology

2012

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This article is written from an organic chemist's point of view and provides an up-to-date review about organic solar cells based on small molecules or oligomers as absorbers and in detail deals with devices that incorporate planar-heterojunctions (PHJ) and bulk heterojunctions (BHJ) between a donor (p-type semiconductor) and an acceptor (n-type semiconductor) material. The article pays particular attention to the design and development of molecular materials and their performance in corresponding devices. In recent years, a substantial amount of both, academic and industrial research, has been directed towards organic solar cells, in an effort to develop new materials and to improve their tunability, processability, power conversion efficiency, and stability. On the eve of commercialization of organic solar cells, this review provides an overview over efficiencies attained with small molecules/oligomers in OSCs and reflects materials and device concepts developed over the last decade. Approaches to enhancing the efficiency of organic solar cells are analyzed.

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“…das terminal mit Fluorenon verknüpfte Sexithiophen 69 vor und setzten es als Donormaterial in BHJ‐Solarzellen ein. Die Zellen, die mit einem 1:1‐Blend (w/w) aus 69 und 160 hergestellt wurden, erreichten maximale PCEs von etwa 0.8 % bei AM1.5, 100 mW cm −2 Beleuchtung 122…”

Section: Lösungsprozessierte Bhj‐solarzellen Aus Niedermolekularenunclassified

Niedermolekulare organische Halbleiter auf dem Vormarsch – Ausblick auf künftige Solartechniken

2012

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Wir bieten hier aus der Sicht von Organikern einen aktuellen Überblick über organische Solarzellen, deren Absorberschicht auf niedermolekularen Molekülen oder Oligomeren basiert, und behandeln im Detail Planar‐Heteroübergangs‐ sowie Bulk‐Heteroübergangs‐Solarzellen mit organischen Donor‐ (p‐Halbleiter) und Akzeptormaterialien (n‐Halbleiter). Dabei liegt das Hauptaugenmerk auf dem Design und der Entwicklung von molekularen Materialien und auf deren Leistung in entsprechenden Solarzellen. In den vergangenen Jahren wurde in großem Umfang akademische und industrielle Forschung in Richtung organischer Solarzellen betrieben. Kurz vor der geplanten Kommerzialisierung von organischen Solarzellen liefern wir hier einen Überblick über Effizienzen, die bisher in solchen Solarzellen erzielt wurden, und präsentieren Materialien und Solarzellenkonzepte, die in den letzten zehn Jahren entwickelt wurden. Darüber hinaus werden Ansätze zur Erhöhung der Effizienz von organischen Solarzellen analysiert.

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Synthesis and characterisation of fluorenone–thiophene-based donor–acceptor oligomers: role of moiety sequence upon packing and electronic properties

Cited by 34 publications

References 47 publications

Alternating Copolymers Based on 2,1,3‐Benzothiadiazole and Hexylthiophene: Positioning Effect of Hexyl Chains on the Photophysical and Electrochemical Properties

Alternating Copolymers Based on 2,1,3‐Benzothiadiazole and Hexylthiophene: Positioning Effect of Hexyl Chains on the Photophysical and Electrochemical Properties

Small Molecule Organic Semiconductors on the Move: Promises for Future Solar Energy Technology

Niedermolekulare organische Halbleiter auf dem Vormarsch – Ausblick auf künftige Solartechniken

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