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

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

• Premansh Dudhe,
• Mena Asha Krishnan,
• Kratika Yadav,
• Diptendu Roy,
• Krishnan Venkatasubbaiah,
• Biswarup Pathak and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

• traces of any β-carboline product were observed, which proves that the heterocyclization reaction is highly regiospecific. Optical properties of γ-carbolines Interestingly, the γ-carboline derivatives were found to be highly fluorescent under UV light irradiation. A systematic literature survey revealed

• that the structural core of carbolines had been widely exploited for the development of organic fluorescent entities, and in general, their UV absorbance ranges between 340 to 380 nm. For a deeper insight into the optical properties of the novel substituted γ-carbolines, absorption and emission studies

Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles

• Mio Matsumura,
• Takahiro Teramoto,
• Masato Kawakubo,
• Masatoshi Kawahata,
• Yuki Murata,
• Kentaro Yamaguchi,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2021, 17, 671–677, doi:10.3762/bjoc.17.56

• and derivatization of trivalent phosphole F and the optical properties have not been clarified. The systematic knowledge of the properties of a new family of fused phospholes is valuable for the design of new types of functional π-electron-containing materials. This paper presents the synthesis

• , molecular structure, and optical properties of 6-phenyl-6H-benzo[f]naphtho[2,3-b]phosphoindole (F) and the derivatives in which the phosphorus atom is chemically modified, such as a phospholium salt and the borane–phosphine complex. Results and Discussion Treatment of 3,3′-dibromo-2,2′-binaphthyl (1) [21

Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF₃)₂CHOH]

• Takeshi Fujita,
• Noriaki Shoji,
• Nao Yoshikawa and
• Junji Ichikawa

Beilstein J. Org. Chem. 2021, 17, 396–403, doi:10.3762/bjoc.17.35

• ]helicenes was possible, in which no serious decrease in yield was observed in Suzuki–Miyaura coupling and cycloaromatization (see the Experimental section) [30]. Next, double helical compounds were set as synthetic targets, because their unique optical properties have recently attracted much attention [5

Control over size, shape, and photonics of self-assembled organic nanocrystals

• Chen Shahar,
• Yaron Tidhar,
• Yunmin Jung,
• Haim Weissman,
• Sidney R. Cohen,
• Ronit Bitton,
• Iddo Pinkas,
• Gilad Haran and
• Boris Rybtchinski

Beilstein J. Org. Chem. 2021, 17, 42–51, doi:10.3762/bjoc.17.5

• - and morphology-dependent properties arising from confinement effects and strong interactions between neighboring atoms [1][2][3]. The correlation between nanoparticle size and the related electronic and optical properties has extensively been studied, leading to applications in novel technologies and

Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring

• Daria I. Tonkoglazova,
• Anna V. Gulevskaya,
• Konstantin A. Chistyakov and
• Olga I. Askalepova

Beilstein J. Org. Chem. 2021, 17, 11–21, doi:10.3762/bjoc.17.2

• alternating enantiomers form a screw along the a axis. Optical properties All helicenes 10 are well soluble in dichloromethane and chloroform. Solubility in other common solvents such as acetonitrile, DMSO, tetrahydrofuran, ethanol and hexane is markedly lower. Carbazole-based [6]helicene 12 was described as

Construction of pillar[4]arene[1]quinone–1,10-dibromodecane pseudorotaxanes in solution and in the solid state

• Xinru Sheng,
• Errui Li and
• Feihe Huang

Beilstein J. Org. Chem. 2020, 16, 2954–2959, doi:10.3762/bjoc.16.245

• of G on the optical properties of H, so an UV–vis spectroscopy experiment was carried out. We investigated the changes in the UV–vis absorption of the complex at different guest concentrations corresponding to 0.5 and 1 equiv. As shown in Figure 4, the concentration of G did not affect the absorption

Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives

• Jonas Becher,
• Daria V. Berdnikova,
• Heiko Ihmels and
• Christopher Stremmel

Beilstein J. Org. Chem. 2020, 16, 2795–2806, doi:10.3762/bjoc.16.230

• bound to the G4-DNA, such as fluorescent light-up effects and the formation of ICD bands, which are mostly pronounced with linker length of n = 4 (with a2) and n = 5 (with 22AG). This significant influence of the complex structure on the optical properties of the ligand provides some evidence that each