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

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

• Hengjia Liu and
• Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

• spectrum (see Figure 9b), which were different from the same chemical environment of fluorine atoms in the original B(C6F5)3. To further explore the interaction of the Lewis acid–base pairs, Huang et al. added B(C6F5)3 to pyridine group-capped diketopyrrolopyrrole (DPP) molecules, i.e., DPPPy-Py-F (16

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

• a diketopyrrolopyrrole fragment in a mixture with PC71BM showed a record efficiency of 5.86% among oligomeric isoindigo [17]. At the same time, similarly constructed (D–A–D–A) oligomers 6 in the composition with PC71BM showed an efficiency of 1.3–1.4% [18]. Another way to design isoindigoid OSCs is

[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

• synthesized [163]. A synthesis of C60 fullerene conjugate 214 with a benzothiadiazole moiety is shown in Scheme 45, while Scheme 46 presents a synthetic pathway to diketopyrrolopyrrole-modified conjugate 215. Other methanofullerenes without aromatic groups obtained by this method are presented below

• fullerene array 213. The synthetic route to conjugates 214 of fullerene with benzothiadiazole. The synthetic route to conjugates 215 of fullerene with diketopyrrolopyrrole. The synthetic route to fullerene–acetylene hybrids. [60]PCBM derivatives containing various aromatic and alkyl groups bound to the C60

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

• Engineering, Czestochowa University of Technology, Armii Krajowej 17, Czestochowa, 42-200, Poland 10.3762/bjoc.13.235 Abstract Nine new quadrupolar chromophores based on diketopyrrolopyrrole were designed and prepared by cross-coupling reactions. The property tuning has been achieved by structural variation

• generation. The experimental data were completed by quantum-chemical calculations and structure–property relationships were elucidated. Keywords: calculations; diketopyrrolopyrrole; electrochemistry; electronic spectra; push–pull; third-harmonic generation; Introduction Known for more than 40 years

• and 3b/4b) and are not capable to properly calculate organometallic ferrocene derivatives 5b. However, this is its common feature [45][46]. Conclusion In conclusion, we have designed a series of diketopyrrolopyrrole derivatives having D–π–A–π–D arrangement. Nine new chromophores were conveniently and

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

• (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

• (40–60 nm). Keywords: bulk heterojunction; diketopyrrolopyrrole; organic solar cells; star-shaped oligomers; tetrathienoanthracene; Introduction Solution-processable organic semiconductors have been intensively studied as key materials for low-cost, flexible, and large-area optoelectronic devices

• -accepting diketopyrrolopyrrole (DPP) arms, and its linear analogue, TTA-DPP4 and TTA-DPP2 (Figure 1). TTA can be regarded as a promising central core unit for star-shaped π-conjugated oligomers, and has previously been utilized as a building block of semiconducting polymers for OSCs [24] and organic field

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

• Diego Cortizo-Lacalle,
• Calvyn T. Howells,
• Upendra K. Pandey,
• Joseph Cameron,
• Neil J. Findlay,
• Anto Regis Inigo,
• Tell Tuttle,
• Peter J. Skabara and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

• Physics & Astronomy, University of St. Andrews, St. Andrews, KY16 9SS, UK Interdisciplinary Centre for Energy Research, Indian Institute of Science, Bangalore 560012, India 10.3762/bjoc.10.283 Abstract Two novel triads based on a diketopyrrolopyrrole (DPP) central core and two 4,4-difluoro-4-bora-3a,4a

• the triads, theoretical DFT and TDDFT calculations were performed. Keywords: BODIPY; diketopyrrolopyrrole; organic semiconductors; organic solar cells; thiophene; Introduction The discovery of photoinduced electron transfer from conjugated polymers to fullerene (C60), and the favourable

• derivatives (e.g., selenophene) [20][21][22][23], often in combination with other heterocyclic units; the best performing systems are push–pull molecules or dyes [14]. In the last few years the diketopyrrolopyrrole (DPP, 1, Figure 1) core has been widely incorporated in conjugated polymers for both OPVs and

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

• Bernd Tieke A. Raman Rabindranath Kai Zhang Yu Zhu Department of Chemistry, University of Cologne, D-50939 Cologne, Germany 10.3762/bjoc.6.92 Abstract Research activities in the field of diketopyrrolopyrrole (DPP)-based polymers are reviewed. Synthetic pathways to monomers and polymers, and the

• characteristic properties of the polymers are described. Potential applications in the field of organic electronic materials such as light emitting diodes, organic solar cells and organic field effect transistors are discussed. Keywords: conjugated polymer; diketopyrrolopyrrole; electroluminescence