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Search for "electron accepting" in Full Text gives 70 result(s) in Beilstein Journal of Organic Chemistry.

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

  • Shakeel Alvi and
  • Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

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  • corresponding trimethylsumanene 28 by means of nucleophilic oxidation using NaHMDS in the presence of molecular oxygen in DMF as the solvent (Scheme 8). It has been noticed from the literature that the directly linked π-conjugated systems act as promising electron-accepting materials because of their high LUMO
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Published 09 Sep 2020

Natural dolomitic limestone-catalyzed synthesis of benzimidazoles, dihydropyrimidinones, and highly substituted pyridines under ultrasound irradiation

  • Kumar Godugu,
  • Venkata Divya Sri Yadala,
  • Mohammad Khaja Mohinuddin Pinjari,
  • Trivikram Reddy Gundala,
  • Lakshmi Reddy Sanapareddy and
  • Chinna Gangi Reddy Nallagondu

Beilstein J. Org. Chem. 2020, 16, 1881–1900, doi:10.3762/bjoc.16.156

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  • groups, such as electron-donating groups (4-Me: 2b, 4-OMe: 2e, and 3,4,5-trimethoxy: 2g), an electron-accepting group (4-NO2: 2l), and halogen atoms (4-F: 2m, 4-Cl: 2n, and 3-Br: 2s), respectively, at different positions on the aromatic ring displayed a good reactivity with malononitrile (8) and
  • ), 3,4-dimethoxy (2f), 3-OH (2r), and 2-OH (2h), respectively, at different positions on the ring reacted well with ethyl acetoacetate (4) and urea (5) to produce the products, 7b–f in good isolated yields that ranged from 92–96% (Table 6, entries 2–6). A benzaldehyde derivative with an electron
  • -accepting nitro group (2l) at the para position on the ring showed a good reactivity with ethyl acetoacetate (4) and urea (5) to afford the product 7g in an excellent isolated yield (94%, Table 6, entry 7). Halogen atoms at different positions on the ring of benzaldehyde derivatives (4-F: 2m, 4-Cl; 2n, and
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Published 03 Aug 2020

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

  • Rasa Keruckiene,
  • Simona Vekteryte,
  • Ervinas Urbonas,
  • Matas Guzauskas,
  • Eigirdas Skuodis,
  • Dmytro Volyniuk and
  • Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

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  • . As shown in Figure 2, the LUMOs were located on the central electron-accepting quinazoline core and the phenyl unit, whereas the HOMOs were mainly localized on the electron-donating peripheral substituents. The HOMO energy values (Table 1) showed dependence on the donating characteristics of the
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Published 28 May 2020

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

  • Nuray Altinolcek,
  • Ahmet Battal,
  • Mustafa Tavasli,
  • William J. Peveler,
  • Holly A. Yu and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93

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  • homoleptic or heteroleptic iridium(III) complexes were also reported in the construction of different OLEDs [10][11][12][13]. In OPVs, carbazole derivatives are frequently used as small molecule p-type (electron-donating) materials or electron-accepting (n-type) materials with a variety of donor–acceptor
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Published 19 May 2020

Aryl-substituted acridanes as hosts for TADF-based OLEDs

  • Naveen Masimukku,
  • Dalius Gudeika,
  • Oleksandr Bezvikonnyi,
  • Ihor Syvorotka,
  • Rasa Keruckiene,
  • Dmytro Volyniuk and
  • Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 989–1000, doi:10.3762/bjoc.16.88

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  • the incorporation of electron-accepting and electron-donating moieties into the same molecule [18][19]. Conventional hosts such as 1,3-bis(N-carbazolyl)benzene (mCP) and bis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO), are generally used as hosts in blue phosphorescent OLEDs, are also widely
  • , Figure 4b, and Table 2). The IPPES values were further used for constructing OLED structures. The highest IPPES of 5.62 eV was obtained for compound 6 which contains electron-accepting fluorine atoms. The other compounds (3–5) demonstrated similar IPPES values mainly attributed to removing an electron
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Published 13 May 2020

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

  • Phil M. Pithan,
  • Sören Steup and
  • Heiko Ihmels

Beilstein J. Org. Chem. 2020, 16, 904–916, doi:10.3762/bjoc.16.82

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  • have shown that depending on the nature of the metal ion, the adopted position relative to the nitrogen and oxygen atoms may vary [82]. In 3a and 3b, the electron density of the phenolate oxygen atom was significantly reduced due to the direct conjugation with the strong electron-accepting
  • Knoevenagel reaction from the readily available 5-formyl-substituted spirooxazine 1b. Due to the introduction of the electron-accepting quinolizinium(ethenyl) substituent, the spirooxazines 3a and 3b were photoinert towards the electrocyclic ring opening, thus constituting one of the rare cases of
  • Phil M. Pithan Soren Steup Heiko Ihmels Department of Chemistry and Biology, University of Siegen and Center of Micro- and Nanochemistry and Engineering (Cμ), Adolf-Reichwein-Str. 2, 57068 Siegen, Germany 10.3762/bjoc.16.82 Abstract Two new spiroindolinonaphthoxazine derivatives with an electron
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Published 05 May 2020

Synthesis, liquid crystalline behaviour and structure–property relationships of 1,3-bis(5-substituted-1,3,4-oxadiazol-2-yl)benzenes

  • Afef Mabrouki,
  • Malek Fouzai,
  • Armand Soldera,
  • Abdelkader Kriaa and
  • Ahmed Hedhli

Beilstein J. Org. Chem. 2020, 16, 149–158, doi:10.3762/bjoc.16.17

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  • standard. The oxadiazole moieties are thought to be responsible for the majority of the dipole moment in the prepared compounds. Due to the electron-donating effect of alkyl groups in combination with the electron-accepting oxadiazole [35], the prepared hydrocarbon compounds are expected to perform dipole
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Published 31 Jan 2020

Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

  • Daniel R. Sutherland,
  • Nidhi Sharma,
  • Georgina M. Rosair,
  • Ifor D. W. Samuel,
  • Ai-Lan Lee and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2019, 15, 2914–2921, doi:10.3762/bjoc.15.285

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  • were calculated from the optimized ground-state structure using the Tamm Dancoff approximation (TDA) to time-dependent density functional theory (TD-DFT) [30][31]. In all derivatives, the LUMO is mainly localized on the strongly electron-accepting BQ moiety (Figure 3). The HOMO is mainly located on the
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Published 04 Dec 2019

Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence

  • Vânia F. Pais,
  • Tristan Neumann,
  • Ignacio Vayá,
  • M. Consuelo Jiménez,
  • Abel Ros and
  • Uwe Pischel

Beilstein J. Org. Chem. 2019, 15, 2612–2622, doi:10.3762/bjoc.15.254

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  • , boron with sp2 hybridization, such as in triarylboranes, offers the possibility to modulate fluorescence properties by the addition of Lewis bases (e.g., fluoride ions [27][28][29][30][31]) or by exploring the electron-accepting properties of the boron, including charge-transfer and photoinduced
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Published 04 Nov 2019

1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss

  • Arnault Heynderickx,
  • Sébastien Nénon,
  • Olivier Siri,
  • Vladimir Lokshin and
  • Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2019, 15, 2059–2068, doi:10.3762/bjoc.15.203

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  • –C8–N9 atom chains and the respective bond lengths of the second independent molecule of 3 reveals a contribution of the intramolecular charge transfer from the electron donating ethylenediamino moiety (D) toward the electron accepting ethylenediimino (A) moiety as shown by the narrow range of the C–N
  • -donating ethylenediamino moiety toward the electron-accepting ethylenediimino moiety in 3 and delocalization of the positive charges in 6a and 7a (Scheme 3), and are not artifacts arising from the strong intermolecular interactions within the crystals. Losing aromaticity, the benzene ring is becoming less
  • −···N+ distances being 3.184 and 3.042 Å, respectively. These interactions, as well as intramolecular charge transfer from the electron-donating ethylenediamino moiety to the electron-accepting ethylenediimino moiety give rise to a certain degree of the single and double bond lengths equalization. Thus
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Published 28 Aug 2019

Synthesis, photophysical and electrochemical properties of pyridine, pyrazine and triazine-based (D–π–)2A fluorescent dyes

  • Keiichi Imato,
  • Toshiaki Enoki,
  • Koji Uenaka and
  • Yousuke Ooyama

Beilstein J. Org. Chem. 2019, 15, 1712–1721, doi:10.3762/bjoc.15.167

Graphical Abstract
  • and OUJ-2 with two (diphenylamino)carbazole thiophene units as D (electron-donating group)–π (π-conjugated bridge) moiety and a pyridine, pyrazine or triazine ring as electron-withdrawing group (electron-accepting group, A) have been designed and synthesized. The photophysical and electrochemical
  • an electron-donating group (D) such as a diphenyl or dialkylamino group and an electron-withdrawing group (electron-accepting group, A) such as a nitro, cyano, and carboxy group or an azine ring such as pyridine, pyrazine and triazine linked by π-conjugated bridges such as oligoenes and heterocycles
  • electron-donating and electron-accepting abilities of the D and A moieties and the expansion of π conjugation, respectively, can lead to a decrease in the energy gap between the HOMO and LUMO because the highest occupied molecular orbital (HOMO) is localized over the π-conjugated system containing the D
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Published 22 Jul 2019

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

  • Yu-Ying Wang,
  • Yong Kong,
  • Zhe Zheng,
  • Wen-Chao Geng,
  • Zi-Yi Zhao,
  • Hongwei Sun and
  • Dong-Sheng Guo

Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139

Graphical Abstract
  • systemic delivery; “super”-quenching minimizes the imaging background and phototoxicity to normal tissues [27]. The complexation of GC5A with ICT dyes 1,8-ANS and 2,6-TNS are considered involving ICT processes in their photophysics [40][41] because of their intramolecular electron-donating and electron
  • -accepting structures. An increase in charge separation within ICT probes would occur upon excitation which results in a larger dipole moment in the excited state. The energy of the excited state with a larger dipole moment could be reduced by interaction with a high polarity environment and could be
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Published 25 Jun 2019

Diaminoterephthalate–α-lipoic acid conjugates with fluorinated residues

  • Leon Buschbeck,
  • Aleksandra Markovic,
  • Gunther Wittstock and
  • Jens Christoffers

Beilstein J. Org. Chem. 2019, 15, 981–991, doi:10.3762/bjoc.15.96

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  • are colored materials (yellow, orange, or red) showing pronounced fluorescence in solution (Table 1). The absorption and emission wavelengths are sensitively tuned by the electron-accepting or electron-donating nature of the nitrogen-substituents at the aromatic ring. In Table 1, compound 1 with an
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Published 26 Apr 2019

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

  • Aude-Héloise Bonardi,
  • Frédéric Dumur,
  • Guillaume Noirbent,
  • Jacques Lalevée and
  • Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

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  • molecule. 1.3.3 Charge transfer transition (CT): A charge transfer transition is mostly observed from interaction between the LUMO on an electron accepting group and the HOMO on an electron-donating group. This can be an intermolecular or intramolecular process. For an intramolecular process, this type of
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Published 12 Dec 2018

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes

  • Cristina Cebrián and
  • Matteo Mauro

Beilstein J. Org. Chem. 2018, 14, 1459–1481, doi:10.3762/bjoc.14.124

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Published 18 Jun 2018

Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis

  • Yue Pan,
  • Kunfang Jia,
  • Yali Chen and
  • Yiyun Chen

Beilstein J. Org. Chem. 2018, 14, 1215–1221, doi:10.3762/bjoc.14.103

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  • -donating 3,4-dimethoxy groups. Cyclic voltammetry measurements were also carried out for BI-alkynes 3a–f, in which the reduction potential (Ep re) indicated the electron-accepting capacity of the BI-alkynes. As expected, the reduction potential of 3a was increased with electron-deficient 3,4-difluoro
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Published 28 May 2018

Recent advances on organic blue thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs)

  • Thanh-Tuân Bui,
  • Fabrice Goubard,
  • Malika Ibrahim-Ouali,
  • Didier Gigmes and
  • Frédéric Dumur

Beilstein J. Org. Chem. 2018, 14, 282–308, doi:10.3762/bjoc.14.18

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  • a suitable steric hindrance that introduces an internal twist and interrupts the π-conjugation but also by a sufficient distance between the electron-donating and the electron-accepting moieties [22][23][24][25]. In the design of TADF materials, it should be mentioned the major importance of the
  • problem is commonly observed if the isolation of the electron-donating and electron-accepting parts is obtained upon extension of the distance between the two moieties. Indeed, as a consequence of this strategy, a weaker intramolecular charge transfer takes place and a reduction of the oscillator strength
  • same conditions. The spatial separation of the electron-donating part from the electron-accepting moiety by elongating the spacer has already been discussed and the drawbacks evoked. Minimization of the electron density overlap can also be realized by means of an ortho-phenyl linkage, enabling to
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Published 30 Jan 2018

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

  • Jan Podlesný,
  • Lenka Dokládalová,
  • Oldřich Pytela,
  • Adam Urbanec,
  • Milan Klikar,
  • Numan Almonasy,
  • Tomáš Mikysek,
  • Jaroslav Jedryka,
  • Iwan V. Kityk and
  • Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

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  • -emitting diodes (OLED), fluorophores, probes for ion sensing, functional polymers, and more recently also chromophores with nonlinear optical (NLO) activity. The latter property is mostly dictated by their conjugated character, electron-accepting behavior of the DPP scaffold, strong emissive character, and
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Published 08 Nov 2017

Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives

  • Mio Matsumura,
  • Mizuki Yamada,
  • Atsuya Muranaka,
  • Misae Kanai,
  • Naoki Kakusawa,
  • Daisuke Hashizume,
  • Masanobu Uchiyama and
  • Shuji Yasuike

Beilstein J. Org. Chem. 2017, 13, 2304–2309, doi:10.3762/bjoc.13.226

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  • electron-accepting properties. This red shift related to methylation of a phosphorus atom is in line with other earlier studies [10][18][33]. The fluorescence intensity of 7 (Ф = 67%) was as strong as that of phosphine oxide 4. The gold and boron complexes (8 and 9, respectively) showed contrasting
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Published 30 Oct 2017

Metal-free hydroarylation of the side chain carbon–carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid

  • Anna S. Zalivatskaya,
  • Dmitry S. Ryabukhin,
  • Marina V. Tarasenko,
  • Alexander Yu. Ivanov,
  • Irina A. Boyarskaya,
  • Elena V. Grinenko,
  • Ludmila V. Osetrova,
  • Eugeniy R. Kofanov and
  • Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2017, 13, 883–894, doi:10.3762/bjoc.13.89

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  • aromatic ring of the styryl group of oxadiazoles 1 play a crucial role for the protonation and reactivity of these compounds. Thus, styryl-substituted oxadiazoles 1b,c and substrates 1f–k, bearing electron-accepting halogen substituents, need higher reaction temperatures up to 60 °C (Table 2, entries 4, 8
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Published 11 May 2017

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

  • Stephen Hill and
  • M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

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  • to improve the PL properties of CDs, the use of boron as an additive, which is an electron-accepting element, has also been explored by Hao et al. [38]. The CDs were produced by the addition of boric acid (B(OH)3) into the hydrothermal carbonisation of glucose, using a Teflon autoclave at 180 °C for
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Published 10 Apr 2017

Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles

  • Anastasia S. Kostyuchenko,
  • Tatyana Yu. Zheleznova,
  • Anton J. Stasyuk,
  • Aleksandra Kurowska,
  • Wojciech Domagala,
  • Adam Pron and
  • Alexander S. Fisyuk

Beilstein J. Org. Chem. 2017, 13, 313–322, doi:10.3762/bjoc.13.34

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  • frequently combine solution processability with unique electronic, luminescent and electrochemical properties [1][2][3][4][5]. Molecules in which a central electron-accepting ring separates two bithiophene units are of particular interest [6][7][8][9][10][11][12][13][14][15]. The continuing progress in this
  • , solution-processable and conjugated compounds can be modified in a controllable way by the nature of the electron-accepting heterocyclic ring, the position of the solubilizing alkyl substituent and the molecule topology (linear vs three-arms star) [16][19][21][23]. In particular, the synthesized molecules
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Published 17 Feb 2017

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

  • David R. Chisholm,
  • Garr-Layy Zhou,
  • Ehmke Pohl,
  • Roy Valentine and
  • Andrew Whiting

Beilstein J. Org. Chem. 2016, 12, 1851–1862, doi:10.3762/bjoc.12.174

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  • temperatures. Coupling these strongly electron-donating scaffolds to electron-accepting moieties caused the resulting structures to exhibit strong fluorescence. Keywords: cyclisation; dihydroquinoline; elimination; reduction; tetrahydroquinoline; Introduction Tetrahydroquinolines (THQ) and dihydroquinolines
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Published 16 Aug 2016

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

  • Hideaki Komiyama,
  • Chihaya Adachi and
  • Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

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  • (OPERA), Kyushu University 10.3762/bjoc.12.142 Abstract Solution-processable star-shaped and linear π-conjugated oligomers consisting of an electron-donating tetrathienoanthracene (TTA) core and electron-accepting diketopyrrolopyrrole (DPP) arms, namely, TTA-DPP4 and TTA-DPP2, were designed and
  • acceptor–donor–acceptor electronic structures, an electron-donating TTA unit was coupled with electron-accepting diketopyrrolopyrrole (DPP)-based chromophoric units, which are well-known building blocks used in OSCs [28][29][30][31]. Such molecular structures facilitate intramolecular charge transfer
  • nm) originating from intramolecular charge transfer (ICT) transitions between the electron-donating TTA and the electron-accepting DPP units. Evidently, the maximum absorption coefficient (ε) of TTA-DPP4 (22.3 × 104 M−1 cm−1) is more than twice that of TTA-DPP2 (9.6 × 104 M−1 cm−1), which is
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Published 14 Jul 2016

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic–organic hybrid perovskite solar cells

  • Wei Li,
  • Munechika Otsuka,
  • Takehito Kato,
  • Yang Wang,
  • Takehiko Mori and
  • Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2016, 12, 1401–1409, doi:10.3762/bjoc.12.134

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  • a UV-O3 cleaner (Filgen, Model UV253E) for 20 min. The electron-accepting TiO2 compact layer was spin-coated (1500 rpm for 30 s) from a mildly acidic (after addition of 12 μM HCl) solution of titanium(IV) isopropoxide in anhydrous ethanol and sintered at 120 °C for 10 s. The mesoporous TiO2 layer
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Published 07 Jul 2016
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