Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• ). Single crystal X-ray diffraction data could be obtained for three DPQDs. One reveals pairwise hydrogen bonding in the solid state as well as a herringbone packing arrangement rendering it a promising candidate for additional studies in the context of organic optoelectronic devices. Keywords: conjugated

• molecules; N-heteroacenes; hydrogen bonding; optoelectronic properties; organic field-effect transistors; organic semiconductors; Introduction The role of weak intermolecular interactions in tuning the properties of organic semiconductors has garnered significant attention in the past two decades, owing to

Enhanced host–guest interaction between [10]cycloparaphenylene ([10]CPP) and [5]CPP by cationic charges

• Eiichi Kayahara,
• Yoshiyuki Mizuhata and
• Shigeru Yamago

Beilstein J. Org. Chem. 2024, 20, 436–444, doi:10.3762/bjoc.20.38

• -conjugated molecules, CPPs with shorter conjugations have lower oxidation potentials than larger CPPs, and the first and the second oxidation potentials of [5]CPP are by 0.69 and 0.51 V lower than those of [10]CPP, respectively [43]. The other is the stability of the CPP dications. Since the dications are

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

• guaranteeing long-lived CS states. Guldi et al. synthesized 16 distinct donor–acceptor conjugated molecules, denoted as 89–104 (Figure 11). These molecules comprised ZnP as an electron donor and push–pull chromophores with varying reduction potentials as electron acceptors interconnected by various rigid

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

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

• linear azaacene structures but also non-linear structures as shown in Scheme 13. This versatility allowed for a broader range of conjugated molecules to be successfully prepared. The target azaacene analogues 62–64, featuring 2,6-(CH3)2C6H3 groups were obtained in yields ranging from 50 to 85% through a

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

• Valentin H. K. Fell,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Eman J. Hussien and
• Peter J. Skabara

Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

• -conjugated ring structures [15]. In the solid state, fused systems are prone to form highly ordered π–π-stacked structures [16], leading to better bulk charge transport [17]. Another important aspect is solubility, which is generally poor in larger conjugated molecules [3]. This is even aggravated for fused

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

• the addition of suitable Lewis acids can lead to a dramatic red-shift in the absorption and emission of the mixtures. The electrophilic Lewis acid as electron acceptor frequently reacts with the nitrogen-containing heterocyclic conjugated molecules, ascribed to the charge redistributions of the

Tetraphenylethylene-embedded pillar[5]arene-based orthogonal self-assembly for efficient photocatalysis in water

• Zhihang Bai,
• Krishnasamy Velmurugan,
• Xueqi Tian,
• Minzan Zuo,
• Kaiya Wang and
• Xiao-Yu Hu

Beilstein J. Org. Chem. 2022, 18, 429–437, doi:10.3762/bjoc.18.45

• chromophoric dye molecules can be utilized in photoredox reactions under the irradiation of light with suitable wavelength [6]. However, in the case of the m-TPEWP5G-EsY nanosystem, which contains conjugated molecules and displays harvesting antenna effects from ultraviolet to visible light wavelengths, solar

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli,
• Noureddine Chaaben,
• Kamel Alimi,
• Stefan Jopp and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

• molecules have been examined. Additionally, theoretical studies based on density functional theory (DFT/B3LYP/6-31G(d)) were carried out. Keywords: alkynes; catalysis; cross-coupling; heterocycles; palladium; Introduction The development and design of small π-conjugated molecules have attracted increasing

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

• monoiodosumanene 79, which was prepared via an alternate route using 6,6’-diiodo-2,2’-dimethoxy-1,1’-binaphthol in the presence of Sc(OTf)3. The Suzuki-coupling reaction between 1-pyreneboronic acid and iodosumanene 79 furnished the desired compound 93 in 84% yield (Scheme 22). Among the bowl-shaped π-conjugated

• molecules, sumanene is more attractive as chemical modifications can be easily performed at both benzylic as well as peripheral aromatic carbons. Although, a handful of reports are available in the literature related to the selective functionalization at the benzylic carbons of the sumanene. In contrast

Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules

• Shigeyuki Yamada,
• Takuya Higashida,
• Yizhou Wang,
• Masato Morita,
• Takuya Hosokai,
• Kaveendra Maduwantha,
• Kaveenga Rasika Koswattage and
• Tsutomu Konno

Beilstein J. Org. Chem. 2020, 16, 1154–1162, doi:10.3762/bjoc.16.102

• deactivation process from the lowest singlet (S1) excited state to the ground (S0) state [9]. Interestingly, for such π-conjugated molecules, suitable structural modifications can switch the radiative S1→S0 process to another radiative deactivation process from the triplet (T1) excited state to S0 via an S1→T1

Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes

• Aya Yoshimura,
• Hitoshi Kimura,
• Kohei Kagawa,
• Mayuka Yoshioka,
• Toshiki Itou,
• Dhananjayan Vasu,
• Takashi Shirahata,
• Hideki Yorimitsu and
• Yohji Misaki

Beilstein J. Org. Chem. 2020, 16, 974–981, doi:10.3762/bjoc.16.86

• bearing 1,3-dithiol-2-ylidenes took place efficiently to produce the corresponding π-conjugated molecules. We also succeeded in the estimation of the oxidation potentials and number of electrons involved in each oxidation step of the obtained compounds by digital simulations. Keywords: cross-conjugated

• -dithiole rings, which are of interest as novel multistage redox systems as well as donor components for organic conductors [1][31][32][33][34][35][36][37][38][39][40][41]. The palladium-catalyzed C–H arylation might offer access to new cross-conjugated molecules bearing vinyl-extended TTF moieties (EBDTs

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

• Vladimir A. Burilov,
• Guzaliya A. Fatikhova,
• Mariya N. Dokuchaeva,
• Ramil I. Nugmanov,
• Diana A. Mironova,
• Pavel V. Dorovatovskii,
• Victor N. Khrustalev,
• Svetlana E. Solovieva and
• Igor S. Antipin

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

• the aggregate. Therefore, a different packing of aggregates is the main reason for the observed ADP/ATP selectivity of calixarene 10b. Polydiacetylene–10b vesicles for ADP/ATP sensing Polydiacetylenes (PDAs), alternating ene-yne conjugated molecules, induce a blue-to-red color transition by the

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

• Fabio Tonin and
• Isabel W. C. E. Arends

Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33

• , for example, deoxycholic acid (DCA), LCA and UDCA. Secondary bile acids can be subsequently resorbed and returned to the liver where they are re-secreted in a process known as enterohepatic circulation. In mammals, bile acids are secreted as conjugated molecules with glycin or taurine (Figure 2

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

• observed in D–A–D-type conjugated molecules [28]. DFT calculations To gain a deeper understanding of the electronic and photophysical properties of the synthesized 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles we have performed quantum-chemical calculations for four

Effect of the π-conjugation length on the properties and photovoltaic performance of A–π–D–π–A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-b:4,5-b′]dithiophene core

• Ni Yin,
• Lilei Wang,
• Yi Lin,
• Jinduo Yi,
• Lingpeng Yan,
• Junyan Dou,
• Hai-Bo Yang,
• Xin Zhao and
• Chang-Qi Ma

Beilstein J. Org. Chem. 2016, 12, 1788–1797, doi:10.3762/bjoc.12.169

• . China Department of Chemistry, Xi’an Jiaotong Liverpool University, 111 Ren Ai Road, Dushu Lake Higher Education Town, Suzhou, Jiangsu, 215123, P. R. China 10.3762/bjoc.12.169 Abstract Benzo[1,2-b:4,5-b′]dithiophene (BDT) is an excellent building block for constructing π-conjugated molecules for the

• -bridges have better power conversion efficiency and higher device stability. The device based on the quaterthiophene-bridged compound 4 gave a highest power conversion efficiency of 5.62% with a VOC of 0.93 V, JSC of 9.60 mA·cm−2, and a FF of 0.63. Keywords: A–π–D–π–A-type conjugated molecules

• molecular structure and properties of the conjugated molecules with BDT core, we report here a series of A–π–D–π–A-type conjugated molecules with a regioregular oligo(3-hexylthiophene) chain as the π-bridge unit. The optical and electrochemical properties of these compounds were systematically investigated

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

• -OSCs. The design of star-shaped π-conjugated molecules offers possibilities for not only further enhancement of the photoabsorption ability but also for the improvement of molecular packing, solubility, and film-forming ability. However, the impact of star-shaped molecular structures on optoelectronic

Supramolecular chemistry: from aromatic foldamers to solution-phase supramolecular organic frameworks

• Zhan-Ting Li

Beilstein J. Org. Chem. 2015, 11, 2057–2071, doi:10.3762/bjoc.11.222

• (SIOC). In the spring of 1985, the second semester of the fourth year, I entered Professor Zhendong Chen’s lab to perform my dissertation research. I stayed in the lab for about three months and prepared several ferrocene-derived conjugated molecules to study the homologous linearity [1]. I later

Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp²)–H bond arylations

• Fatiha Abdelmalek,
• Fazia Derridj,
• Safia Djebbar,
• Jean-François Soulé and
• Henri Doucet

Beilstein J. Org. Chem. 2015, 11, 2012–2020, doi:10.3762/bjoc.11.218

• of heteroarylated polyfluorobiphenyls in good yields via two or three sequential iterative palladium-catalyzed direct arylations. Different pathways for the synthesis of π-conjugated molecules incorporating fluorinated phenylene units. i) Pd(OAc)2, KOAc, DMA, 150 °C. ii) PdCl(C3H5)(dppb), KOAc, DMA

Synthesis and spectroscopic properties of β-triazoloporphyrin–xanthone dyads

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2015, 11, 1434–1440, doi:10.3762/bjoc.11.155

• -diethynylxanthen-9-one. In addition, a new series of various β-triazole-linked porphyrin–xanthone conjugates and xanthone-bridged triazoloporphyrin dyads were synthesized through click chemistry in moderate to good yields. The preliminary photophysical evaluation of these π-conjugated molecules revealed a

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin

• Jun Terao,
• Yohei Konoshima,
• Akitoshi Matono,
• Hiroshi Masai,
• Tetsuaki Fujihara and
• Yasushi Tsuji

Beilstein J. Org. Chem. 2014, 10, 2800–2808, doi:10.3762/bjoc.10.297

• , this method can only be applied to the synthesis of insulated oligo(phenylene–ethylene) monomers. To synthesize other insulated π-conjugated molecules, we became interested in another insulation technique to replace this self-inclusion: full rotation of the glucopyranose units of methylated

• synthesis of symmetrically insulated π-conjugated molecules with pseudo linked [3]rotaxane structure via flipping of a glucopyranose unit of permethylated β-cyclodextrin. In this method, oligo(para-phenylene), oligothiophene, and porphyrin derivatives were used as π-conjugated guests. After cross-coupling

Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins

• Satyasheel Sharma and
• Mahendra Nath

Beilstein J. Org. Chem. 2013, 9, 496–502, doi:10.3762/bjoc.9.53

• of a new series of dihydro-1,3-oxazinoporphyrins in moderate to good yields. These novel porphyrin-dihydro-1,3-oxazine hybrids may be considered as potential candidates not only for biological evaluations but also for the development of newer π-conjugated molecules for various material applications

Symmetrical and unsymmetrical α,ω-nucleobase amide-conjugated systems

• Sławomir Boncel,
• Maciej Mączka,
• Krzysztof K. K. Koziol,
• Radosław Motyka and
• Krzysztof Z. Walczak

Beilstein J. Org. Chem. 2010, 6, No. 34, doi:10.3762/bjoc.6.34

• ]. Moreover, α,ω-nucleobase amide-conjugated molecules possess the tendency to form meta-stable complexes with DNA and thus can perturb the cell replication. For example, amide-linked heterodimer synthons consisting of acyclic nucleoside units and 5′-amino-2′,5′-dideoxythymidine are PNA/DNA chimeras (V) [4

Novel loop-like aromatic compounds: a further step on the road to nanobelts and nanotubes

• Venkataramana Rajuri,
• Dariush Ajami,
• Gaston R. Schaller,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2010, 6, No. 30, doi:10.3762/bjoc.6.30

• ; tetradehydrodianthracene; Introduction The first loop-like (in plane) conjugated molecules [1][2] prepared by rational synthesis were reported 13 years ago [3][4][5]. Unlike “normal” cyclic conjugated rings with p orbitals perpendicular to the ring plane such as benzene, the p orbitals of belt-like conjugated structures

Low temperature enantiotropic nematic phases from V-shaped, shape-persistent molecules

• Matthias Lehmann and
• Jens Seltmann

Beilstein J. Org. Chem. 2009, 5, No. 73, doi:10.3762/bjoc.5.73

• the bisector. Reflections (ii) correspond to a distance which can be rationalised by the separation of two antiparallel thiadiazole rings along the molecular long axis. Reflections (iii) are typical for the π–π distance between conjugated molecules. Note that for reflections (i) and (iii) the