Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

• Recep Isci and
• Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

• triphenylamine as donor and dimesitylboron as acceptor linked through a thieno[3,2-b]thiophene (TT) π-conjugated linker bearing a 4-MeOPh group, was designed, synthesized, and fabricated as an emitter via a solution process for an organic light-emitting diode (OLED) application. DMB-TT-TPA (8) exhibited

• absorption. A solution-processed OLED was fabricated using low turn-on voltage, which had performances with maximum power, current, and external quantum efficiencies of 6.70 lm/W, 10.6 cd/A, and 4.61%, respectively. Keywords: OLED; organoboron; solution processes; thienothiophene; triphenylamine

• layers are composed of various aromatic π-conjugated small molecules/polymers including thiophene, anthracene, carbazole, and triphenylamine [9][10][11][12][13]. Thienothiophenes are two annulated thiophene rings having four isomers, among which the most widely used isomer is thieno[3,2-b]thiophene (TT

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry

• Koji Kubota,
• Emiru Baba,
• Tamae Seo,
• Tatsuo Ishiyama and
• Hajime Ito

Beilstein J. Org. Chem. 2022, 18, 855–862, doi:10.3762/bjoc.18.86

• bearing relatively large conjugated structures (1f−m) tended to show low reactivity under the optimized conditions at 60 °C, but the reactions proceeded smoothly at 110 °C. For example, the bromo-substituted triphenylamine (1f), pyrene (1g and 1h), fluoranthene (1i), biphenyl (1j), triphenylene (1k

Recent advances in the application of isoindigo derivatives in materials chemistry

• Andrei V. Bogdanov and
• Vladimir F. Mironov

Beilstein J. Org. Chem. 2021, 17, 1533–1564, doi:10.3762/bjoc.17.111

• ][121]. In this field, a number of condensed derivatives of oligoisoindigo 68–70, triphenylamine-containing monoisoindigo 71, and selenophenevinylene polymer 72 were investigated (Scheme 32). In terms of photothermal conversion (62–71% yield), ribbon-like compounds turned out to be the most effective

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• , the structures of 4,4'-diphenylfullerene derivatives synthesized are shown in Figure 11, and a number of diphenylmethanofullerenes 169–177 with electron-withdrawing groups are reported in reference [148] (Figure 12). Publication [149] describes compound 178 containing triphenylamine donor groups

• ]. Typical procedure for a synthesis of [60]PCBM derivatives. The synthetic route to triphenylamine-substituted methanofullerene 178. The synthetic route to water-soluble methano[60]fullerene-appended tetracarboxylic acid derivatives. The synthetic route to diarylmethanofullerene 183. The synthetic route to

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

• donor 4,4′,4″-tris[3-methylphenyl(phenyl)amino]triphenylamine. A white OLED based on these versatile exciplex systems with a relatively high maximum brightness of 3030 cd/m2 and an external quantum efficiency of 0.5% was fabricated. Keywords: carbazole; dimethyldihydroacridine; exciplex; phenothiazine

• peaked at the wavelength of 592 nm was observed for the solid mixture with the donor 4,4′,4″-tris[3-methylphenyl(phenyl)amino]triphenylamine (m-MTDATA) (Figure 7b). The combination of the sky-blue and orange exciplex emissions may result in white electroluminescence (EL). To check this assumption, a non

• )amino]triphenylamine. A white OLED was fabricated based on the versatile exciplex-forming systems with a relatively high maximum brightness of 3030 cd/m2 and an EQE of 0.5%. Experimental Instrumentation 1H NMR and 13C NMR spectra were recorded with a Bruker Avance III apparatus (400 and 101 MHz). The

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

• this in mind, we targeted donor (D)–phenylene–acceptor (A) systems that would be of potential interest to the organic semiconductor community. These compounds incorporate strong donors in the form of triphenylamine (TPA) and carbazole (Cz), as can be seen in Scheme 1. Since the corresponding

Functional panchromatic BODIPY dyes with near-infrared absorption: design, synthesis, characterization and use in dye-sensitized solar cells

• Quentin Huaulmé,
• Cyril Aumaitre,
• Outi Vilhelmiina Kontkanen,
• David Beljonne,
• Alexandra Sutter,
• Gilles Ulrich,
• Renaud Demadrille and
• Nicolas Leclerc

Beilstein J. Org. Chem. 2019, 15, 1758–1768, doi:10.3762/bjoc.15.169

• spacer [14][21][23][24]. Introduction of such units on those positions is known to lead to a larger bathochromic shift of the S0→S1 absorption band than the same substitution on its 2nd and 6th positions [25]. A thiophene-triphenylamine unit was selected among the reported electron-donating units, due to

• functional theory (TD-DFT) calculations on the four representative molecules displayed in Figure 2: Dyes (1 and 3) vs (2 and 4) differ by the position (2,6 or 1,7) of the methyl groups on the BODIPY core, while dyes (1 and 2) vs (3 and 4) differ by the presence (or not) of a triphenylamine donor group on the

• ) Grafting the triphenylamine donor moieties on the thiophene-vinylene bridge only slightly (by ca. 0.1 eV) lowers the ionization potential of the dyes, compare (1,2) to (3,4); this is explained by the fact that the HOMO molecular orbital mostly spreads on the BODIPY-vinylthiophene core of the molecules

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• copolymer synthesized by Friedel–Crafts alkylation of triphenylamine (115) with dibromo-p-xylene 112 was prepared (Scheme 21). After the sulfonation process, the resulted material has been employed as a heterogeneous, reusable, and environmentally benign catalyst in the multicomponent synthesis of

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

• fabricated OLEDs using phosphor 13 as emitting layer was ITO (100 nm)/TAPC (80 nm)/4,4’,4’’-tri(9-carbazoyl)triphenylamine (TCTA) (10 nm)/Pt(fppz)2 neat (30 nm)/1,3-bis(3,5-di(pyridin-3-yl)phenyl)benzene (BMPYPB) (15 nm)/BMPYPB:1 wt % Rb2CO3 (40 nm)/Al (100 nm). These devices exhibited an outstanding EQE

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

• triarylboron moieties as acceptors. As possible donors, diarylamines have often been proposed (carbazole, triphenylamine, carbazole/triphenylamine hybrids, 9,9-dimethyl-9,10-dihydroacridine), as exemplified in Figure 2 [34][35][36]. In B1 and B2, isolation of the two parts was obtained by linking the 10H

• be realized by totally blocking the structure, what was done with B9 and B10 in which two of the three aromatic rings of triphenylamine were connected to the boron center [39]. By elongating the π-conjugation of the electron-donating group in B10 compared to B9, a more delocalized HOMO level could be

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

• -photon absorbers (2PA). In this respect, the central DPP bicyclic lactam is often decorated with electron donors such as alkoxy- or dialkylamino groups [11][12], triphenylamine [13][14], heterocyclic carbazole [15], thiophene [16][17], furan [18], and organometallic ferrocene [19]. 2PA-active DPPs were

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

• their extended dimensionality, in comparison to their linear analogues. Star-shaped π-conjugated molecules consisting of hexa-peri-hexabenzocoronene [8][9][10][11][12][13][14], pyrene [15][16][17], and triphenylamine [18][19][20][21][22][23] central cores have been developed as donor materials for BHJ

New core-pyrene π structure organophotocatalysts usable as highly efficient photoinitiators

• Sofia Telitel,
• Frédéric Dumur,
• Thomas Faury,
• Bernadette Graff,
• Mohamad-Ali Tehfe,
• Didier Gigmes,
• Jean-Pierre Fouassier and
• Jacques Lalevée

Beilstein J. Org. Chem. 2013, 9, 877–890, doi:10.3762/bjoc.9.101

• , Py_3, Py_4, Py_9, Py_10) two functionalized triazines (Py_7, Py_12), a triphenylamine (Py_6), a carbazole (Py_11) and a benzothiadiazole (Py_8) (Scheme 3). The idea is to get a high absorption around 380–410 nm where Xe–Hg lamps, Xe lamps, LED, laser diodes and even household halogen lamps are usable

Ring-opening reaction of 2,5-dioctyldithieno[2,3-b:3',2'-d]thiophene in the presence of aryllithium reagents

• Hao Zhong,
• Jianwu Shi,
• Jianxun Kang,
• Shaomin Wang,
• Xinming Liu and
• Hua Wang

Beilstein J. Org. Chem. 2013, 9, 767–774, doi:10.3762/bjoc.9.87

• be completed at −78 °C. Similar to the case of 2e bearing the EDG group of triphenylamine, 2h also gave a good yield of 3h (76%, Table 1, entry 8). These results indicate that an increase of the electron donating character of the substituted aryl groups leads to a higher nucleophilicity of the

Cation affinity numbers of Lewis bases

• Christoph Lindner,
• Raman Tandon,
• Boris Maryasin,
• Evgeny Larionov and
• Hendrik Zipse

Beilstein J. Org. Chem. 2012, 8, 1406–1442, doi:10.3762/bjoc.8.163

• than the one in amines. This implies that phosphanes have a more pyramidal structure than amines with a comparable substitution pattern. The least pyramidal structure is found here for triphenylamine, which is almost perfectly planar at the nitrogen atom. The degree of planarity correlates well with

Conjugated polymers containing diketopyrrolopyrrole units in the main chain

• Bernd Tieke,
• A. Raman Rabindranath,
• Kai Zhang and
• Yu Zhu

Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92

• ]. The polymers consisted of dialkylated DPP units and carbazole, triphenylamine, benzo[2,1,3]thiadiazole, anthracene, or fluorene units in alternating fashion. They were prepared via Suzuki coupling, from the DPP monomers M-1 or DPP-3,6-diphenyl(4,4´-bis(pinacolato)boron ester. A number of readily

Prediction of reduction potentials from calculated electron affinities for metal-salen compounds

• Sarah B. Bateni,
• Kellie R. England,
• Anthony T. Galatti,
• Handeep Kaur,
• Victor A. Mendiola,
• Alexander R. Mitchell,
• Michael H. Vu,
• Benjamin F. Gherman and
• James A. Miranda

Beilstein J. Org. Chem. 2009, 5, No. 82, doi:10.3762/bjoc.5.82

• whether a potential substituted triphenylamine was likely to have a high enough oxidation potential to be useful as an electrocatalyst for a difficultly oxidized organic substrate before embarking upon a proposed synthesis of the substituted triphenylamine. By using Fry’s method of calculating EAs to