Donor/acceptor-substituted anthradithiophene materials: synthesis, optical and electrochemical properties

Balandier, Jean‐Yves; Quist, Florence; Sebaïhi, Noham; Niebel, Claude; Tylleman, Benoît; Boudard, Pol; Bouzakraoui, Saïd; Lemaur, Vincent; Cornil, Jérôme; Lazzaroni, Roberto; Geerts, Yves; Stas, Sara

doi:10.1016/j.tet.2011.06.098

Cited by 6 publications

(10 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Acenes can react with oxygen by either electron‐transfer (Type I) or energy‐transfer mechanisms (Type II), and both types are believed to operate simultaneously whenever the acene is excited by irradiation (cf. our investigations) . The oxidation process, as already mentioned, primarily leads to endoperoxides, which may reproduce the acenes upon thermolysis or photolysis .…”

Section: Introductionsupporting

confidence: 58%

“…Photochemical stability from seconds to hours has been reported in the literature for various acenes, and it depends, primarily, on the structure of the acene, the presence or absence of oxygen, water, and adsorbents, as well as on the volume of the photon energy delivered to the sample by various light sources . For acenes exposed to low‐energy light sources, an increase in their light resistance to days has been observed.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Mono‐Aryl/Alkylthio‐Substituted (Hetero)acenes of Exceptional Thermal and Photochemical Stability by the Thio‐Friedel–Crafts/Bradsher Cyclization Reaction

Bałczewski

Kowalska

Różycka‐Sokołowska

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

The highly substituted mono‐aryl/alkylthio‐(hetero)acenes prepared in this study have been found to be thermally more stable (Tdecomp.=331–354 °C) than the known di‐aryl/alkylthio‐substituted acenes by an average of 25 °C. They are also much more photostable at 254 and 365 nm (in both argon and air) than the parent anthracene and other reported anthracenes. The most photostable aryl/alkylthio‐anthracenes at 254 nm were found to be 60–70 (in air) and 130 (in argon) times more stable in solution than the unsubstituted anthracene, and much more stable than known EDG/EWG‐substituted anthracenes (EDG=electron‐donating group, EWG=electron‐withdrawing group) with an extended aromatic core. Furthermore, the acenes showed significantly higher photostability at 365 nm in both air and argon. The anthracenes were obtained by the novel thio‐Friedel–Crafts/Bradsher cyclization reaction of hitherto unknown [o‐(1,3‐dithian‐2‐yl)aryl](aryl)methyl thioethers. The developed approach provides a general access to mono‐aryl/alkylthio‐substituted (hetero)acene frameworks containing at least three fused (hetero)aromatic rings. The characteristic feature of this approach, which leads to highly substituted acenes, is that the substituents, unlike in other methods, may be introduced at an early stage of the synthesis. DFT and TD‐DFT calculations confirmed the stabilizing role of the aryl/alkylthio substituent in the mono‐aryl/alkylthio‐substituted anthracenes, which are the most stable anthracenes prepared to date. Their high photostability is mainly due to the quenching of singlet oxygen by the acene and the quenching of the acene S1 state by molecular oxygen.

show abstract

Section: Introductionsupporting

confidence: 58%

Section: Introductionmentioning

confidence: 99%

Mono‐Aryl/Alkylthio‐Substituted (Hetero)acenes of Exceptional Thermal and Photochemical Stability by the Thio‐Friedel–Crafts/Bradsher Cyclization Reaction

Bałczewski

Kowalska

Różycka‐Sokołowska

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…The general synthetic routes for monomers and copolymers are shown in Scheme . Compound 2 was synthesized starting from thiophene‐2,3‐dicarbaldehyde in two steps, similar to the method described for 2,8‐dioctyl‐5,11‐di(thiophen‐2‐yl)anthra[2,3‐b:6,7‐b′]dithiophene by Balandier et al Trimethyltin moieties were attached to compound 2 to compound 3 in 55% yield.…”

Section: Resultsmentioning

confidence: 99%

“…The onset potentials for oxidation ( E ox ) are observed to be 0.89 V, 1.00 V, 0.91 eV for PADTDPP, PADTTPD, and PADTFBO, respectively. The ADT monomers usually show obvious oxidation waves at 0.3–0.6V . These waves are ascribed to the oxidation of copolymers into their corresponding radical‐cation species.…”

Section: Resultsmentioning

confidence: 99%

“…Solvents for the reactions and photophysical measurements were all distilled after dehydration according to conventional methods. Anthra[2,3‐b:6,7‐b′]dithiophene‐5,11‐dione, 3,6‐bis(5‐bromothiophen‐2‐yl)‐2,5‐bis(2‐octyldecyl)pyrrolo[3,4‐c]pyrrole‐1,4(2H,5H)‐dione (DPP), and 4,7‐bis(5‐bromofuran‐2‐yl)‐5,6‐bis(octyloxy)benzo[c][1,2,5] oxadiazole (FBO) were prepared according to the procedures described in the literature.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Photovoltaic Properties of New Multifused Anthradithiophene‐Based Narrow‐Bandgap D–A Copolymers

Liu

Peng

Chen

et al. 2014

Macro Chemistry & Physics

View full text Add to dashboard Cite

Three structurally novel donor–acceptor copolymers are synthesized and fully characterized using an anthradithiophene (ADT) derivative as the donor block. All of them exhibit broad absorption ranges and moderate hole and electron mobilities. The multifused ADT donor block makes them exhibit lower highest occupied molecular orbital (HOMO) energy levels than many reported benzodithiophene‐based polymers. Copolymer blends with [6,6]‐phenyl C71 butyric acid methyl ester (PC71BM) as active layers are used to fabricate polymer solar cells (PSCs) and a variety of post‐treatment methods are employed to optimize the device performance. The conventional and inverted configuration devices are prepared to evaluate the photovoltaic properties. A maximum power conversion efficiency of 1.66% is achieved for the inverted‐configuration device. The improved efficiency is caused by the close energy alignment between the work function of MoO3 and the HOMO energy levels of the copolymers, facilitating better charge transport and increased short‐circuit current density (Jsc) with the inverted devices.

show abstract

Synthesis of Annulated Anthracenes, Carbazoles, and Thiophenes Involving Bradsher‐Type Cyclodehydration or Cyclization–Reductive‐Dehydration Reactions

et al. 2015

View full text Add to dashboard Cite

show abstract

Donor/acceptor-substituted anthradithiophene materials: synthesis, optical and electrochemical properties

Cited by 6 publications

References 44 publications

Mono‐Aryl/Alkylthio‐Substituted (Hetero)acenes of Exceptional Thermal and Photochemical Stability by the Thio‐Friedel–Crafts/Bradsher Cyclization Reaction

Mono‐Aryl/Alkylthio‐Substituted (Hetero)acenes of Exceptional Thermal and Photochemical Stability by the Thio‐Friedel–Crafts/Bradsher Cyclization Reaction

Synthesis and Photovoltaic Properties of New Multifused Anthradithiophene‐Based Narrow‐Bandgap D–A Copolymers

Synthesis of Annulated Anthracenes, Carbazoles, and Thiophenes Involving Bradsher‐Type Cyclodehydration or Cyclization–Reductive‐Dehydration Reactions

Contact Info

Product

Resources

About

Donor/acceptor-substituted anthradithiophene materials: synthesis, optical and electrochemical properties

Cited by 6 publications

References 44 publications

Mono‐Aryl/Alkylthio‐Substituted (Hetero)acenes of Exceptional Thermal and Photochemical Stability by the Thio‐Friedel–Crafts/Bradsher Cyclization Reaction

Mono‐Aryl/Alkylthio‐Substituted (Hetero)acenes of Exceptional Thermal and Photochemical Stability by the Thio‐Friedel–Crafts/Bradsher Cyclization Reaction

Synthesis and Photovoltaic Properties of New Multifused Anthradithiophene‐Based Narrow‐Bandgap D–A Copolymers

Synthesis of Annulated Anthracenes, Carb­azoles, and Thiophenes Involving Bradsher‐Type Cyclodehydration or Cycli­zation–Reductive‐Dehydration Reactions

Contact Info

Product

Resources

About

Synthesis of Annulated Anthracenes, Carbazoles, and Thiophenes Involving Bradsher‐Type Cyclodehydration or Cyclization–Reductive‐Dehydration Reactions