Synthesis of Highly Soluble and Oxidatively Stable Tetraceno[2,3-<i>b</i>]thiophenes and Pentacenes

Palayangoda, Sujeewa S.; Mondal, Rajib; Shah, Bela; Neckers, Douglas C.

doi:10.1021/jo0710331

Cited by 50 publications

(29 citation statements)

References 18 publications

(23 reference statements)

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“…Anthony and co‐workers popularized the use of diethynyl acenes, including pentacenes, which show superior optoelectronic properties and are both highly soluble and stable 11–16. The stability of diethynylpentacenes is at least in part due to physical quenching of singlet oxygen ( 1 O 2 ), cycloaddition with which is a major decomposition pathway of most pentacenes,17 by these materials 18.…”

Section: Methodsmentioning

confidence: 99%

Combining Electronic and Steric Effects for Highly Stable Unsymmetric Pentacenes

Zhang

Pawle

Haas

et al. 2014

Chemistry A European J

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This paper describes the reactivity of unsymmetrically substituted pentacenes to photochemical oxidation. Acenes in general, and pentacenes in particular, are a key family of compounds for a variety of organic electronics applications. The instability of many pentacene derivatives, particularly to oxidation, is an important restriction in their applicability. Several substitution strategies for decreasing the reactivity of pentacene exist, but these almost always involve symmetrically substituted derivatives, restricting the chemical space of structures from which to choose. In this paper, we demonstrate that combining electronic and steric effects yields highly stable unsymmetrically substituted pentacenes.

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Section: Methodsmentioning

confidence: 99%

Combining Electronic and Steric Effects for Highly Stable Unsymmetric Pentacenes

Zhang

Pawle

Haas

et al. 2014

Chemistry A European J

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“…[14] Withr espect to longer acenes, Neckers and co-workers described highly substituted,p hotostable pentacenes and tetracenothiophenes that combine two ethynyl groups on the central ring of these compounds with two methoxy groups on an adjacentr ing. [15] Other insights have included dialkoxytetracene derivatives that undergo [4+ +4] photodimerizations, [4b] and 6,13-dialkoxypentacenes with HOMO-LUMO gaps of % 2.0-2.1 eV. [16] Given the importance of acenes with more than three fused rings in optoelectronic devices,i ncluding their rapid reactivity with 1 O 2 ,i na ddition to the unique influences of alkoxy groups on acene chemistry,o ur objective here is to understand the relationship between the chemicals tructures, spectroscopy,a nd reactivities of dialkoxyacenes.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopy and Reactivity of Dialkoxy Acenes

Brega

Kanari

Doherty

et al. 2019

Chemistry A European J

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Photochemical oxidation of acenes can benefit or impedet heir function, depending on the application.A lthougha cenes with alkoxy substituents on reactive sites are important for applications as diverseasdrug delivery and organic optoelectronics, the influence of chemical structure on their photochemical oxidation remainsu nknown. This paper therefore describes the synthesis, spectroscopic properties, and reactivity with singlet oxygen ( 1 O 2 )o faseries of dialkoxyacenest hat varyi nt he number and types of fused rings in the (hetero)acene cores. Reductive alkylationofquinone precursorsy ieldedt arget dialkoxyacenesw ith fused backbones rangingf rom benzodithiophene to tetracenothiophene. Trends of their experimental spectroscopicc haracteristics were consistent with time-dependent density functional theory( TD-DFT) calculations.N MR studies show that photochemically generated 1 O 2 oxidizes all but one of these acenest ot he corresponding endoperoxidesi no rganic solvent. The rates of these oxidations correlate with the number and types of fused arenes,w ith longer dialkoxyacenesg enerally oxidizing faster than shorterd erivatives. Finally,i rradiation of these acenes in acidic, oxidizing environmentsc leavest he ether bonds. This work impacts those workingi no rganic optoelectronics, as well as those interested in harnessing photogenerated reactive oxygen speciesi n functional materials.[a] Dr.

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“…Most organic sensitizers absorb light below 600 nm while reasonably efficient near-IR/IR dyes used in DSSCs are only occasionally seen in literature. [24][25][26][27][28][29] Pentacene chromophores, with potential absorption out to 750 nm, 30 could extend the window of performance for DSSCs, provided that there is efficient coupling between the acene and the inorganic matrix. We report here the synthesis of a series of pentacene dyes ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Functionalized pentacenes for dye-sensitized solar cells

Shankar

Mor

et al. 2011

J. Photon. Energy

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Abstract. Carboxylic acid functionalized pentacene-based dyes are synthesized and tested in dye-sensitized solar cells utilizing titania (rutile) nanowire arrays as the electron transporting photoanode. Functionalization on both chromophore and solubilizing substitutents leads to materials demonstrating promising light-harvesting and energy-conversion properties in these large polycyclic aromatic compounds. C 2011 Society of Photo-Optical Instrumentation Engineers (SPIE).

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Synthesis of Highly Soluble and Oxidatively Stable Tetraceno[2,3-b]thiophenes and Pentacenes

Cited by 50 publications

References 18 publications

Combining Electronic and Steric Effects for Highly Stable Unsymmetric Pentacenes

Combining Electronic and Steric Effects for Highly Stable Unsymmetric Pentacenes

Spectroscopy and Reactivity of Dialkoxy Acenes

Functionalized pentacenes for dye-sensitized solar cells

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