Die entwicklung eines neuen photochromen strukturprinzips basierend auf der reversiblen photo-oxidation

Schmidt, Reinhard H.; Drews, W.; Brauer, H.‐D.

doi:10.1016/0047-2670(82)87026-3

Cited by 33 publications

(11 citation statements)

References 12 publications

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“…Benzo[1,2,3- kl :4,5,6- k ′ l ′]dixanthene 37.2a and its analogues containing varying patterns of heteroatoms ( 37.2b – e ) and substituents, ,− as well as additional fused rings, were prepared from disubstituted anthraquinones 37.1a – e , following the strategy used for the synthesis of 32.6 (Scheme , for related earlier work, see ref and references therein). Related systems containing additional fused benzene rings were reported by Clar et al ( 6.2 – 3 , section ).…”

Section: Perylenoidsmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.

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Section: Perylenoidsmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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“…Proton affinity of fundamental molecules has been calculated using various MO methods [13]. The proton affinity of a compound X which gives XH + by protonation, (PA (X->XH + )), was estimated by the equation (2) using the heat of formation calculated by semi-empirical MO method such as AM1, PA(X->XH + ) = -∆H f (XH + ) + ∆H f (H + ) + ∆H f (X) (2) where ∆H f (X) and ∆H f (XH + ) are heats of formation of compound X and its protonated species XH + , respectively. Heat of formation of a proton, ∆H f (H + ) is the electronic energy of 1s orbital, 313.51 kcal mol -1 .…”

Section: Effect Of Replacement Of Peripheral Heteroatomsmentioning

confidence: 99%

“…Photooxidation of benzo[1,2,3-kl:4,5,6-k'l']dixan-thene (2a) using visible light produces colorless endoperoxide (1a), and 1a returns to colored 2a by refluxing in toluene [1,2]. Various derivatives of 2a have been synthesized [3].…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study on the Position of Protonation of Benzodixanthene Endoperoxide and its Analogs

達也¹,

澄男²,

賢一³

2002

J. Comput. Aided Chem.

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Colorless endoperoxide (1a) of benzo [1,2,3-kl:4,5,6-k'l']dixanthene (2a) changes into colored 2a in the presence of acid at room temperature. Interaction between 1a and acid was estimated using the AM1 molecular orbital calculation. The calculation shows that 1a reacts with a proton more easily at an endo oxygen atom than at a xanthene oxygen atom, and that the protonated species goes through a carbocation (4a) to give colored 2a. In order to propose novel functional dyes, which change their color more sensitively by the addition of acid, we studied the interaction between protons and the endoperoxides containing nitrogen (1b) or sulfur (1c) instead of oxygen. Nitrogen analog 1b is a hypothetical molecule. The calculated proton affinity of 1b or 1c at peripheral heteroatoms was about 34 kcal mol -1 greater than that of 1a. The deoxygenation of endoperoxide (1) to give 2 is expected to be accelerated by replacement of the peripheral heteroatoms. Replacement of the peripheral heteroatom from oxygen to nitrogen also showed larger proton affinity in case the protonation would take place at the endo oxygen. Such replacement of the peripheral atoms would be effective modification for the acceleration of color forming reaction because of their greater proton affinity.

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“…12 This observation could be explained by a Diels-Alder reaction of the spacer moiety with singlet oxygen. 14 In fact, spacer models 5 and 7 were highly reactive towards oxygen to afford the corresponding endo-peroxides. 12 The structures of P1a, P2a, P1b, and P2b have further been estimated by force-field calculations of the 8-mer models (Fig.…”

mentioning

confidence: 99%

Exact helical polymer synthesis by a two-point-covalent-linking protocol between C₂-chiral spirobifluorene and C₂- or C_s-symmetric anthraquinone monomers

Okuda

Koyama

et al. 2015

Chem. Commun.

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Two types of one-handed exact helical polymers, coil- and screw-shaped polymers, were synthesized by the two-point-covalent-linking protocol using C2-chiral spirobifluorene (SBF) and C2- or C(s)-symmetric anthraquinone spacers. Central to this protocol is a new aromatic ring-forming reaction based on the stepwise reductive cyclization of bis(aryloxy group)-substituted anthraquinone derivatives. The helical structures of the polymers annulated by aromatic skeletons exhibited high thermal stability attributed to the rigid C2-chiral SBF units and the covalently two-point-connected structure.

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Die entwicklung eines neuen photochromen strukturprinzips basierend auf der reversiblen photo-oxidation

Cited by 33 publications

References 12 publications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Theoretical Study on the Position of Protonation of Benzodixanthene Endoperoxide and its Analogs

Exact helical polymer synthesis by a two-point-covalent-linking protocol between C₂-chiral spirobifluorene and C₂- or C_s-symmetric anthraquinone monomers

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Die entwicklung eines neuen photochromen strukturprinzips basierend auf der reversiblen photo-oxidation

Cited by 33 publications

References 12 publications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Theoretical Study on the Position of Protonation of Benzodixanthene Endoperoxide and its Analogs

Exact helical polymer synthesis by a two-point-covalent-linking protocol between C2-chiral spirobifluorene and C2- or Cs-symmetric anthraquinone monomers

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Product

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Exact helical polymer synthesis by a two-point-covalent-linking protocol between C₂-chiral spirobifluorene and C₂- or C_s-symmetric anthraquinone monomers