The improvement of π-conjugation by the lateral benzene of anthracene and naphthalene

Ho, Jau Der; Yu-Hsien, Chen; Chou, Li-Ting; Lai, Po-Wei; Chen, Pin-Sian

doi:10.1016/j.tetlet.2014.08.097

Cited by 9 publications

(4 citation statements)

References 33 publications

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“…The tail of the emission of these derivatives (7-9) stretches further into red, up to 750 nm compared to the other derivatives which end closer to 600 nm, indicating that excitation is more delocalized as the smaller thiophene moiety can conform to a more planar structure compared to the phenyl substituents. 63 The low fluorescence quantum yield is most probably explained by new non-radiative decay pathways that become possible as the rotation around the anthracenethiophene bond is easier than the anthracene-phenyl bond which is substantially more sterically hindered. The lack of an efficient fluorescence state makes these derivatives less useful for applications requiring emissive materials, such as OLEDs or photon-upconversion.…”

Section: Photophysical Characterizationmentioning

confidence: 99%

Photophysical characterization of the 9,10-disubstituted anthracene chromophore and its applications in triplet–triplet annihilation photon upconversion

et al. 2015

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Section: Photophysical Characterizationmentioning

confidence: 99%

Photophysical characterization of the 9,10-disubstituted anthracene chromophore and its applications in triplet–triplet annihilation photon upconversion

et al. 2015

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“…The emission spectra for these derivatives (7-9) display a long tail into the red reaching up to about 750 nm suggesting that the excitation is more delocalized due to the small thiophene substituent having more rotational freedom than the more sterically hindered phenyl substituent. [126] This easier rotation of the thiophene group is likely responsible for opening new non-radiative deactivation pathways, compared to the more bulky phenyl groups, resulting in a substantial lowering of the fluorescence quantum yield. The phenyl-containing compounds display consequently higher Φ f , many of which are close to that of DPA.…”

Section: Probing Modification Possibilities Of the Dpa Annihilatormentioning

confidence: 99%

Photon upconversion through triplet–triplet annihilation

Gray¹

2019

Photochemistry

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The sun is the only renewable energy source that can accommodate humanity's energy needs today and in the foreseeable future. The sunlight reaching the planet's surface is filtrated through the atmosphere, reducing its UV-light intensity in the 300-400 nm range, which indeed can be harmful to life as we know it in too large doses. However, many useful photoreactions require in practice such high-energy UV-photons, like the catalytic splitting of water to oxygen and hydrogen gas or molecular in-bond energy storage through isomerization to produce heat when reverting to the initial state. The efficiency of these applications could be improved with efficient conversion of low-energy visible to high-energy UV-light. One way to achieve this type of photon upconversion (UC) is through the process called Triplet-Triplet Annihilation (TTA) relying on the interaction between two molecules; a sensitizer and an annihilator. The sensitizer absorbs low energy visible photons as input and transfers that energy through Triplet Energy Transfer (TET) to an annihilator. Two triplet-excited annihilators can thereafter perform TTA, merging the energy equivalents of the two low-energy photons to produce one high-energy photon as output. This Thesis is focused on improving the known bimolecular UC system in fluid environment and approaching the ultimate goal of high efficiency UC in solid materials. In the fluid system I demonstrate the employment of thiol-and thioether-based compounds as scavengers for singlet excited oxygen with positive effect on UC efficiency and stability. In an attempt to aid future design and optimization of upconversion system components the anthracene is 9,10-substituted with electron withdrawing or donating groups while its TTA-UC function is evaluated revealing that substitution at para-positions leads to least perturbation of its spectroscopic properties. The ultimate goal is to achieve supramolecular TTA-UC systems capable of efficient intra-molecular TET and TTA processes and unhindered emission of the upconverted photons. As a first step, we focus on the intra-molecular TTA process with oligomers and dendrimers of 9,10-diphenyl anthracene (DPA) which display positive effects on UC efficiency in solid matrix. In the second step the focus is on the intra-molecular TET process where the sensitizerannihilator complexes are explored through Lewis base-acid coupling with orthogonal transition moments for minimum excited state short circuit effect. Additionally, kinetic simulations of the TTA-UC processes are conducted to aid understanding and optimization. Finally, one TTA-UC system is also applied to chemical in-bond energy storage.

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“…Moreover, electrochromic PEDOT derivatives possess fast switching time with high optical contrast [ 28 ]. However, there are a few studies about the applications of furanyl anthracene based organic molecules [ 29 – 31 ]. Recently, we reported that furan-anthracene-furan (DFA) acceptor type structures could be novel small organic molecules for organic solar cell applications [ 32 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene

KALÇIK¹,

KIVRAK²,

Çarbaş³

2022

Turkish Journal of Chemistry

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In this study, a new copolymer, which is a combination of two chemical structure (9,10-di(furan-2-yl)anthracene and 3,4-ethylenedioxythiophene was synthesized via electrochemical synthesis methods in the electrolyte medium of 0.1 M TBAPF 6 /ACN solution. PEDOT homopolymer was also electrosynthesized for comparator experiments of the polymer formations in the same medium. The characterizations of polymers were achieved with general optical and electrochemical characterization techniques. The corresponding electrochromic copolymer shows blue and lilac color in its neutral and oxidized states, respectively. The copolymer has an optical band gap of 1.65 eV and 24% optical contrast at 500 nm with a high coloration efficiency (170 cm 2 /C) and a fast switching time (1.0 s).

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The improvement of π-conjugation by the lateral benzene of anthracene and naphthalene

Cited by 9 publications

References 33 publications

Photophysical characterization of the 9,10-disubstituted anthracene chromophore and its applications in triplet–triplet annihilation photon upconversion

Photophysical characterization of the 9,10-disubstituted anthracene chromophore and its applications in triplet–triplet annihilation photon upconversion

Photon upconversion through triplet–triplet annihilation

Synthesis and characterization of an electrochromic copolymer based on 9, 10-di (furan-2-yl)anthracene and 3,4-ethylenedioxythiophene

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