Synthesis and properties of 6-alkynyl-5-aryluracils

• Ruben Manuel Figueira de Abreu,
• Till Brockmann,
• Alexander Villinger,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

• gives first insights into the optical properties. It was observed that the photophysical properties could be partially modulated by the chosen substituents. Experimental General information Nuclear magnetic resonance spectra (1H/13C/19F NMR) were recorded on a Bruker AVANCE 300 III, 250II, or 500. The

Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

• Victoria M. Alpatova,
• Evgeny G. Rys,
• Elena G. Kononova and
• Valentina A. Ol'shevskaya

Beilstein J. Org. Chem. 2024, 20, 767–776, doi:10.3762/bjoc.20.70

• aromatic substitution; Introduction Porphyrins are available macroheterocyclic compounds which play an important role in diverse areas of scientific research owing to their unique photophysical, electrochemical, and optical properties [1]. They have been widely studied in biomedical applications, as

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

• linked with anilino-TCBD molecules, denoted as 84 and 85, and investigated their optical properties (Figure 9). They observed robust low-energy ICT absorption peaks at 752/753 nm, along with the distinctive high-energy ICT absorption peaks at 470 nm, which are characteristic of anilino-TCBD. Furthermore

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

• were conducted to gather insights into the optoelectronic characteristics of PAH 51. The obtained data revealed that the synthesized compound possesses a unique absorption and emission profile, highlighting its distinctive optical properties (λmax = 470 nm, λmax,em = 470 nm, Φem = 0.12). Biphenylene

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• spectroscopy were used to study the optical properties of the compounds under investigation. For UV–vis absorbance spectra, solutions or films of the compounds were analyzed using an Avantes AvaSpec-2048XL spectrometer, which allowed us to assess the compounds’ absorption characteristics across the ultraviolet

• accurate measurements of the PLQY, shedding light on the efficiency of light emission from the compounds. By employing this comprehensive array of spectroscopic techniques and experimental setups, we obtained a thorough understanding of the optical properties and luminescent characteristics of the studied

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

• absorption and emission maxima of 411 and 520 nm, respectively, with a mega Stokes shift of 109 nm and fluorescence quantum yields both in the solid state (41%) and in solution (86%). The optical properties were supported by computational chemistry using density functional theory for optimized geometry and

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• efficient synthesis of diversely functionalized enamides 16 and 17, demonstrating remarkable tolerance towards various functional groups. In recent years, there has been a surge of research interest in coumarin derivatives due to their notable biological, pharmacological, and optical properties [16]. Zhou

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

• Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

• pharmacological activities [86][87]. Acylhydrazones can exist in either E or Z forms in solution, and they can exhibit good optical properties for applications as photoswitches, in luminescence sensing, and as metallo-assemblies [88][89]. In organic synthesis, acylhydrazones have served as stable imine

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• chlorination effects on the Qx20 series, resulting in four new NFAs, i.e., Qx22–Qx25 (Figure 4). The research revealed the strategic balance between molecular crystallinity, packing, and optical properties. Qx24 and Qx25, with lower steric hindrance in the alkyl side chains, showed slightly decreased

• functionalities, and optimizing the π-conjugated backbone structure of Qxs, significant advancements have been made. These approaches effectively address key concerns and obstacles, resulting in red-shifted absorption and emission maxima, improved nonlinear optical properties, solvatochromism, mechanical

• , indicating the potential for tunable optical properties based on the surrounding environment. The replacement of difluoroquinoxaline with cyanoquinoxaline improved the nonlinear optical properties, highlighting the importance of tailoring electron acceptor strength. Furthermore, the ability to induce changes

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• with the PLQY dropped to 35% due to intermolecular interactions. However, the emission efficiency of the molecule is enhanced in the solid powder form with a PLQY of 64% owing to its AIE nature. To gain more information about the effect of the solvent on the optical properties of TPECNz, the absorption

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• binding guest molecules/ions, but also to undergo unusual transformations, such as metal-induced expansion/contraction. Depending on the design of the particular hybrid, they present unique features involving intriguing redox chemistry, interesting optical properties, and reactivity towards transition

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

• Kathryn M. Wolfe,
• Shahidul Alam,
• Eva German,
• Fahad N. Alduayji,
• Maryam Alqurashi,
• Frédéric Laquai and
• Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

• NMR spectroscopy, mass spectrometry, and elemental analysis. See Supporting Information File 1 for full synthetic and characterization details. Optical properties Using UV–visible spectroscopy, the optical properties for PDIN-FB, PDIN-B, CN-PDIN-FB, and CN-PDIN-FB in both solution and film form were

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• materials used in additive manufacturing. It is also compatible to a photopolymerization process. For example, it can be applied to the photo-3D-printing of silicone resin [83]. The refractive index is one of the most important optical properties and researchers have invested plenty of effort to develop

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• aldehydes and dimedone in chloroform at 65 °C. The optical properties of the newly prepared porphyrins have been investigated by using UV–vis and emission spectroscopy and the results are presented in this paper. Results and Discussion Synthesis The required precursors, copper(II) 2,3-diamino-5,10,15,20

Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• at 90 °C) [36]. It is now well-documented that the incorporation of heteroatoms into the graphene materials or NG molecules can effectively tune their electronic and optical properties. Examples in Scheme 3 show the nitrogen-doped, seco-HBC-based chiral NGs. By introducing a pyrrole ring, Jux and co

Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

• Semyon V. Tsybulin,
• Ekaterina A. Filatova,
• Alexander F. Pozharskii,
• Valery A. Ozeryanskii and
• Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

• theoretical and experimental studies revealed that the side groups of 1,4-diaryl-1,3-butadiynes have a significant impact on their useful characteristics [7][8][9][10][11][12][13][14]. For example, single-molecule conductivity, nonlinear optical properties, and the ability to serve as photosensitizers of

• point of view, cannot have a significant effect on conformational transformations of 5. All differences in optical properties must be of an electronic nature. It is obvious that the same “butadiyne conjugation pathway” (marked in green) is realized in compound 1, while the conjugation chain in monomers

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• well as optical properties. Moreover, the versatility of coumarin hybrids finds numerous applications including fluorescent brightening agents [16], optical sensors [17], organic light emitting diodes [18][19], light harvesting materials [20] and fluorescent probes in biological imaging [21]. Therefore

• , keeping the biological and optical properties of coumarin and porphyrin in mind, in 2015 we reported the synthesis and photophysical studies of β-triazole-bridged porphyrin-coumarin conjugates 11–15 [22] and β-triazolomethyl-linked porphyrin-coumarin dyads 16–20 [23] by using a click reaction approach

Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation

• Ashish Kumar Mazumdar,
• Gyana Prakash Nanda,
• Nisha Yadav,
• Upasana Deori,
• Upasha Acharyya,
• Bahadur Sk and
• Pachaiyappan Rajamalli

Beilstein J. Org. Chem. 2022, 18, 1177–1187, doi:10.3762/bjoc.18.122

• detecting organic acid vapor at ambient conditions is challenging for solid-state detectors. Therefore, developing a solid-state emitter with reversible switching of the optical properties by external stimuli, such as acid and base vapors, is important. As per the recent literature, such sensors are being

• disruption of the molecular conjugation or ICT interactions upon protonation or deprotonation would lead to switching of the optical properties. While there are many reports on acid–based sensors, TADF emitter-based sensors are rare in the literature. In this context, we chose the D–A molecular design to

• to the singlet state via RISC [17][27]. Heteroatom lone-pair electrons are sensitive to acid and, once protonated, to base, which would facilitate the tuning of optical properties in such media [21][22]. Herein, (4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)(pyridin-4-yl)methanone (BPy-pTC) and (4-(9

Synthesis, optical and electrochemical properties of (D–π)₂-type and (D–π)₂Ph-type fluorescent dyes

• Kosuke Takemura,
• Kazuki Ohira,
• Taiki Higashino,
• Keiichi Imato and
• Yousuke Ooyama

Beilstein J. Org. Chem. 2022, 18, 1047–1054, doi:10.3762/bjoc.18.106

• the higher Φfl value of OTT-2 is mainly attributed to the smaller knr value compared with that of OTK-2. The solid-state optical properties of OTK-2 and OTT-2 were investigated by solid-state UV–vis diffuse reflection–photoabsorption and fluorescence spectral measurements, and time-resolved

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

• materials with the introduction of Lewis acids have been frequently observed due to either physical or chemical interactions. In this mini-review, we elaborate how Lewis acids adjust the optical properties and the bandgap of luminescent materials by simple coordination reactions. It is common that

• (C6F5)3 (BCF) to bind to nitrogen atoms at the basic site a of π-conjugated polymer, providing a simple strategy to regulate the optical properties of the A–D–A chromophore with charge transfer excited state properties [28]. In 2019, Wang et al. constructed a novel exciplex system by using the Lewis

Thiophene/selenophene-based S-shaped double helicenes: regioselective synthesis and structures

• Mengjie Wang,
• Lanping Dang,
• Wan Xu,
• Zhiying Ma,
• Liuliu Shao,
• Guangxia Wang,
• Chunli Li and
• Hua Wang

Beilstein J. Org. Chem. 2022, 18, 809–817, doi:10.3762/bjoc.18.81

• carbohelicenes has led to the synthesis of double, triple, quadruple, quintuple, and sextuple molecules, the chiro-optical properties of these molecules, such as their circular dichroism (CD) and circularly polarized luminescence (CPL), have also been widely studied [1][2][3][4][5][6][7][8]. The development of

Substituent effect on TADF properties of 2-modified 4,6-bis(3,6-di-tert-butyl-9-carbazolyl)-5-methylpyrimidines

• Irina Fiodorova,
• Tomas Serevičius,
• Rokas Skaisgiris,
• Saulius Juršėnas and
• Sigitas Tumkevicius

Beilstein J. Org. Chem. 2022, 18, 497–507, doi:10.3762/bjoc.18.52

• , good electrical and optical properties, and easy chemical modification is a desired structural unit in organic structures targeted for numerous applications including organic photovoltaic solar cells (OPV) [12][13][14], organic field-effect transistors (OFETs) [15][16][17], chemical and biosensors [18

Synthesis of a novel aminobenzene-containing hemicucurbituril and its fluorescence spectral properties with ions

• Qingkai Zeng,
• Qiumeng Long,
• Jihong Lu,
• Li Wang,
• Yuting You,
• Xiaoting Yuan,
• Qianjun Zhang,
• Qingmei Ge,
• Hang Cong and
• Mao Liu

Beilstein J. Org. Chem. 2021, 17, 2840–2847, doi:10.3762/bjoc.17.195

• as reactive sites for derivatization, at the same time allowing for formation of coordination or hydrogen bonds with guests, and the aminobenzene unit as a chromophore could improve the optical properties. With this novel macrocycle in hand, the interactions with some metal cations have been

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

• Ilya A. P. Jourjine,
• Lukas Zeisel,
• Jürgen Krauß and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2668–2679, doi:10.3762/bjoc.17.181

• electronic and optical properties [16][17][18][19][20][21], utilized in LEDs, semiconducting polymers, and solar cells. Consequently, synthetic approaches to fluorenones have attracted large interest and numerous methodologically diverse approaches have been published in the past decades. Among these are

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138