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Search for "substituents" in Full Text gives 1684 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Syntheses and medicinal chemistry of spiro heterocyclic steroids

  • Laura L. Romero-Hernández,
  • Ana Isabel Ahuja-Casarín,
  • Penélope Merino-Montiel,
  • Sara Montiel-Smith,
  • José Luis Vega-Báez and
  • Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

Graphical Abstract
  • substituents of the new heterocycle rather than functionalization on C-3 (Scheme 22). Spirothiazolidine steroids Horiuchi et al. introduced a novel synthetic approach for the preparation of steroidal spiro 1,3-thiazolidines from 2α-bromo-3-oxo steroids, exemplified by compound 76 [46]. Initially, treatment of
  • as a 17β-HSD3 inhibitor [42]. The same research group reported a new family of 3-spiromorpholinones derived from ADT bearing hydrophobic substituents [43][62]. The synthetic key step involved a regioselective aminolysis of the oxirane 131 with different ʟ- or ᴅ-amino acids (53–99% yields) to obtain
  • inhibitors of 17β-HSD3 in a microsomal fraction of rat testes. Their androgenic effect on androgen-sensitive cells LAPC-4 was also evaluated. According to the biological results, compounds 134 and 136 with substituents in (S)-configuration were better inhibitors than the (R)-isomers. Furthermore, tertiary
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Published 24 Jul 2024

Ring opening of photogenerated azetidinols as a strategy for the synthesis of aminodioxolanes

  • Henning Maag,
  • Daniel J. Lemcke and
  • Johannes M. Wahl

Beilstein J. Org. Chem. 2024, 20, 1671–1676, doi:10.3762/bjoc.20.148

Graphical Abstract
  • (Table 1, entry 9). The notable influence of steric and electronic parameters of the PG prompted us to investigate a range of sterically diverse alkyl substituents. Interestingly, while only fragmentation products were obtained for methyl and benzyl groups (Table 1, entries 10 and 11), the sterically
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Published 19 Jul 2024

Generation of multimillion chemical space based on the parallel Groebke–Blackburn–Bienaymé reaction

  • Evgen V. Govor,
  • Vasyl Naumchyk,
  • Ihor Nestorak,
  • Dmytro S. Radchenko,
  • Dmytro Dudenko,
  • Yurii S. Moroz,
  • Olexiy D. Kachkovsky and
  • Oleksandr O. Grygorenko

Beilstein J. Org. Chem. 2024, 20, 1604–1613, doi:10.3762/bjoc.20.143

Graphical Abstract
  • } and 1{8}) or showed low conversion (halogenated derivatives 1{9–11}); 4-aminopyrimidines 1{12–16} also demonstrated low conversion; pyridine derivatives with electron-withdrawing substituents (such as NO2 at C-3 or C-5 positions, as well as CN, SO2NH2, or C(O)NH2 at the C-3 atom) did not work
  • }). Some of these results (e.g., on the reactivity of aminopyrimidine derivatives) were in accordance with the previous literature data [21][29]. Meanwhile, electronic effects of the substituents in the amino heterocycle reported in the previous works were somewhat contradictory. Whereas for the NO2 group
  • wide range of aminopyridines, pyrazines, and pyridazines, it worked poorly for aminoazoles, aminopyrimidines, substrates with strong electron-withdrawing groups, and substrates bearing additional dialkylamino or alkoxy substituents. The electronic nature was a major limiting factor for other two
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Published 16 Jul 2024

Benzylic C(sp3)–H fluorination

  • Alexander P. Atkins,
  • Alice C. Dean and
  • Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 1527–1547, doi:10.3762/bjoc.20.137

Graphical Abstract
  • was effective for the stereoselective fluorination of benzylic positions ortho to aldehyde substituents (Figure 9). The choice of a bulky amino, transient, directing group dictated the stereochemical outcome and promoted the C–F reductive elimination through an inner-sphere pathway. A competitive C–O
  • bond formation for substrates bearing primary benzylic positions, attributed to the faster rate of SN2 at the less hindered carbon. The scope was limited to substrates bearing secondary benzylic sites, with various functional groups tolerated. However, substrates bearing electron-donating substituents
  • on the arene were unsuccessful. Without substituents on the ring, aryl C–H activation and subsequent C–O bond formation occurred along with benzylic fluorination (7) (low efficiency). The presence of a p-methoxy group resulted in a switch in selectivity to acyloxylation 8’ as the major product. The
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Published 10 Jul 2024

Primary amine-catalyzed enantioselective 1,4-Michael addition reaction of pyrazolin-5-ones to α,β-unsaturated ketones

  • Pooja Goyal,
  • Akhil K. Dubey,
  • Raghunath Chowdhury and
  • Amey Wadawale

Beilstein J. Org. Chem. 2024, 20, 1518–1526, doi:10.3762/bjoc.20.136

Graphical Abstract
  • who reported a chiral amine-catalysed aza-Michael addition reaction of pyrazolin-5-ones with α,β-unsaturated ketones to access β-(3-hydroxypyrazol-1-yl)ketones (Scheme 1a) [22]. The developed reaction was restricted to α,β-unsaturated ketones with aliphatic substituents (Scheme 1a) [22]. Ji and Wang
  • -ones 2 (Scheme 2, lower part) with diverse substituents (Br, Cl, F, Me or CN) in the para-position of the N-aryl group. These substrates reacted smoothly with α,β-unsaturated ketone 1c and the corresponding products 3cb–cf were obtained in good yields (61–85.5%) and good to excellent
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Published 09 Jul 2024

Electrophotochemical metal-catalyzed synthesis of alkylnitriles from simple aliphatic carboxylic acids

  • Yukang Wang,
  • Yan Yao and
  • Niankai Fu

Beilstein J. Org. Chem. 2024, 20, 1497–1503, doi:10.3762/bjoc.20.133

Graphical Abstract
  • , the incorporation of pyridyl groups that are commonly found in pharmaceutically active compounds are also possible (8). In general, the catalytic efficiency of this new electrophotochemical protocol was found to be relatively independent of the electronic properties of the aryl substituents and the
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Published 03 Jul 2024

Photoswitchable glycoligands targeting Pseudomonas aeruginosa LecA

  • Yu Fan,
  • Ahmed El Rhaz,
  • Stéphane Maisonneuve,
  • Emilie Gillon,
  • Maha Fatthalla,
  • Franck Le Bideau,
  • Guillaume Laurent,
  • Samir Messaoudi,
  • Anne Imberty and
  • Juan Xie

Beilstein J. Org. Chem. 2024, 20, 1486–1496, doi:10.3762/bjoc.20.132

Graphical Abstract
  • different sizes and substituents are tolerated on the aryl aglycon, we decided to replace the aryl aglycon by photoswitchable azobenzene in both O- and S-galactosides (Figure 1B) to investigate their binding affinity and the influence of the photoisomerization on the lectin interaction. The ammonium group
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Published 03 Jul 2024

Bioinformatic prediction of the stereoselectivity of modular polyketide synthase: an update of the sequence motifs in ketoreductase domain

  • Changjun Xiang,
  • Shunyu Yao,
  • Ruoyu Wang and
  • Lihan Zhang

Beilstein J. Org. Chem. 2024, 20, 1476–1485, doi:10.3762/bjoc.20.131

Graphical Abstract
  • rings. The triangles indicate a product having α-substituents. (c) Crystal structure of DH-ER-KR tridomain (PDB ID 8G7W) [24]. DH, KRS, ER, KRC are colored in cyan, pink, yellow, and purple, respectively. The lid of KR catalytic pocket is colored in red. The co-crystallized cofactor is represented as
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Published 02 Jul 2024

Synthesis of 2-benzyl N-substituted anilines via imine condensation–isoaromatization of (E)-2-arylidene-3-cyclohexenones and primary amines

  • Lu Li,
  • Na Li,
  • Xiao-Tian Mo,
  • Ming-Wei Yuan,
  • Lin Jiang and
  • Ming-Long Yuan

Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130

Graphical Abstract
  • ; primary amine; Introduction Aniline derivatives possessing arylmethyl substituents at the ortho position are an important class of amines. They have a wide variety of practical applications, ranging from anti-depression [1], being δ receptor stimulants in analgesic pharmaceuticals [2], to antioxidant
  • of 3-cyclohexanones caused by the strong electron-withdrawing effect, which made 3a as a base rather than a nucleophile under such conditions. The location of substituents was found to affect the product yield greatly, considering that the reactions worked better with 3-cyclohexenones bearing a para
  • good yields. The electronic properties of the substituents, irrespective of their positions on benzylamines, displayed no substantial disparity on the reaction outcomes, leading to the formation of 4ab–ap in 50–80% yields. Both the heteroarylmethylamines and sterically hindered α-methylbenzylamine
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Published 02 Jul 2024

Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl2 and NH4SCN/KSeCN

  • Jialiang Wu,
  • Haofeng Shi,
  • Xuemin Li,
  • Jiaxin He,
  • Chen Zhang,
  • Fengxia Sun and
  • Yunfei Du

Beilstein J. Org. Chem. 2024, 20, 1453–1461, doi:10.3762/bjoc.20.128

Graphical Abstract
  • investigate the effects of different substituents R2 and R3. When the methyl substituent (R2) was replaced with an aryl group, the corresponding thiocyanated products 2l–o could be obtained in acceptable to moderate yields. On the other hand, the method was equally applicable to the substrate bearing two aryl
  • substituents (R2 and R3), albeit the reaction afforded product 2n in a much lower yield, possibly caused by steric congestion. In addition, when the aryl substituent of R1 was replaced with a tert-butyl group, this method also worked well to give product 2o in moderate yield. Notably, when the C3 and C5
  • product 2q in good yield. Furthermore, we turned our attention to the applicability of this protocol for the selenocyanation of the pyrazole skeleton (Scheme 3). Gratifyingly, the method was equally applicable to selenocyanation of pyrazoles bearing various substituents, with the corresponding
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Published 28 Jun 2024

Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction

  • Xiu-Yu Chen,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2024, 20, 1436–1443, doi:10.3762/bjoc.20.126

Graphical Abstract
  • -ynedioate usually gave the expected tricyclic products in good yields. However, the reaction with diethyl but-2-ynedioate afforded products 4p, 4r and 4t in moderate to lower yields. The 5,6- unsubstituted dihydropyridines with various substituents showed marginal effects on the yields. These results
  • though there are four chiral carbon atoms in the products. It can be found that all reactions proceeded smoothly to give the expected polycyclic compounds 6a–k in satisfactory yields. The substituents on the three components showed very little effect on the yields. These results showed that this reaction
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Published 28 Jun 2024

A comparison of structure, bonding and non-covalent interactions of aryl halide and diarylhalonium halogen-bond donors

  • Nicole Javaly,
  • Theresa M. McCormick and
  • David R. Stuart

Beilstein J. Org. Chem. 2024, 20, 1428–1435, doi:10.3762/bjoc.20.125

Graphical Abstract
  • electronic structure (bonding) and molecular structure (geometry) in diarylhalonium salts. We found a periodic trend with respect to the percentage of s- and p-orbital character used by the central atom to bond to the aryl substituents for a series of isoelectronic diaryl chalcogen and diarylhalonium
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Published 27 Jun 2024

Synthesis of substituted triazole–pyrazole hybrids using triazenylpyrazole precursors

  • Simone Gräßle,
  • Laura Holzhauer,
  • Nicolai Wippert,
  • Olaf Fuhr,
  • Martin Nieger,
  • Nicole Jung and
  • Stefan Bräse

Beilstein J. Org. Chem. 2024, 20, 1396–1404, doi:10.3762/bjoc.20.121

Graphical Abstract
  • followed by the addition of diisopropylamine, either in a one-pot synthesis or in two consecutive steps (Table 1). Subsequently, different aliphatic and aromatic substituents were attached to the pyrazole nitrogen by nucleophilic substitution with suitable organohalides 16 and cesium carbonate [3]. Due to
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Published 20 Jun 2024

Synthetic applications of the Cannizzaro reaction

  • Bhaskar Chatterjee,
  • Dhananjoy Mondal and
  • Smritilekha Bera

Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120

Graphical Abstract
  • ). Huang et al. set up a clean crossed-Cannizzaro-aldol reaction strategy of isatin derivatives 88 and 90 with paraformaldehyde under microwave irradiation to furnish 3,3-disubstituted oxindole derivatives 89a–h and 91a–d [92]. The representative 3-hydroxymethyloxindole adducts with varying substituents
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Published 19 Jun 2024

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

  • Mithu Roy,
  • Bitan Sardar,
  • Itu Mallick and
  • Dipankar Srimani

Beilstein J. Org. Chem. 2024, 20, 1348–1375, doi:10.3762/bjoc.20.119

Graphical Abstract
  • in a satisfactory yield. Various hydrocinnamic acids having electron-donating and electron-withdrawing substituents provided the targeted products 3a–c in good yield. Heterocycles containing carboxylic acids also provided the products 3d–g in moderate to good yield. Aliphatic carboxylic acids, under
  • was applicable to various carboxylic acids with electron-donating as well as electron-withdrawing substituents but unfortunately, aliphatic acids were not effective in this reaction. In addition, several control experiments, such as fluorescence quenching and Stern–Volmer studies, were done to analyze
  • terminal arylalkynes bearing electron-donating and electron-withdrawing substituents were well compatible with this method. The procedure is limited to electron-withdrawing and electron-neutral aryl halides. The presence of a conjugated substituent in the p-position of an aryl halide is crucial for
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Published 14 Jun 2024

Rhodium-catalyzed homo-coupling reaction of aryl Grignard reagents and its application for the synthesis of an integrin inhibitor

  • Kazuyuki Sato,
  • Satoki Teranishi,
  • Atsushi Sakaue,
  • Yukiko Karuo,
  • Atsushi Tarui,
  • Kentaro Kawai,
  • Hiroyuki Takeda,
  • Tatsuo Kinashi and
  • Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 1341–1347, doi:10.3762/bjoc.20.118

Graphical Abstract
  • bromoanisole, the corresponding homo-coupling products 3a, 3c–3e were obtained in good yields. In addition, reactions with substrates having halogen substituents also gave the products (3h and 3i) in moderate yields. It is interesting to note, that the reaction using 3-bromofluorobenzene (5h) gave a small
  • amount of 3,3''-difluoro-1,1':3',1''-terphenyl (6h) as side product, that might derive from an SNAr reaction of 3h with the Grignard reagent of 5h. Moreover, bromoxylenes 5m–o also gave the corresponding products 3m–o, respectively, although the position of substituents affected the yields. On the other
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Published 12 Jun 2024

Synthesis of 1,2,3-triazoles containing an allomaltol moiety from substituted pyrano[2,3-d]isoxazolones via base-promoted Boulton–Katritzky rearrangement

  • Constantine V. Milyutin,
  • Andrey N. Komogortsev and
  • Boris V. Lichitsky

Beilstein J. Org. Chem. 2024, 20, 1334–1340, doi:10.3762/bjoc.20.117

Graphical Abstract
  • participation of hydrazones attract special attention. This reaction is a general method for the preparation of 1,2,3-triazoles bearing various substituents at position 2. Wherein, depending on the type of starting heterocycles various functional derivatives are formed. So, the well-known Boulton–Katritzky
  • prepare an array of target 1,2,3-triazoles 4 with allomaltol unit (Scheme 4). It is interesting to note that the recyclization products can be synthesized in good yields employing various starting arylhydrazones 3 both with donor and acceptor substituents at aromatic rings. Besides that, heterocyclic
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Published 11 Jun 2024

Transition-metal-catalyst-free electroreductive alkene hydroarylation with aryl halides under visible-light irradiation

  • Kosuke Yamamoto,
  • Kazuhisa Arita,
  • Masami Kuriyama and
  • Osamu Onomura

Beilstein J. Org. Chem. 2024, 20, 1327–1333, doi:10.3762/bjoc.20.116

Graphical Abstract
  • a methoxy group were transformed into the products in good yields (3la–na). 4-(Trifluoromethoxy)iodobenzene also well participated in this reaction, affording 3oa in 65% yield. Aryl iodides having fluoro and chloro substituents underwent selective C–I bond cleavage to provide monoalkylated products
  • (3ac, 3ad). In addition to styrene derivatives bearing α-substituents and electronically diverse functionalities, indene and 2-vinylpyridine were all compatible with the present electroreductive hydroarylation (3ae–ak). The reaction of iodobenzene with acrylonitrile and 4-chlorostyrene proceeded
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Published 10 Jun 2024

Phenotellurazine redox catalysts: elements of design for radical cross-dehydrogenative coupling reactions

  • Alina Paffen,
  • Christopher Cremer and
  • Frederic W. Patureau

Beilstein J. Org. Chem. 2024, 20, 1292–1297, doi:10.3762/bjoc.20.112

Graphical Abstract
  • , which exploit the redox flexibility of tellurium, especially in the context of phenotellurazine scaffolds. Notably, we showed that phenotellurazine PTeZ1 could significantly catalyze the cross-dehydrogenative phenothiazination of phenols bearing challenging electron-withdrawing substituents under a
  • . In order to further investigate the matter, we next turned our attention to non-heterocyclic tellurethers Te8–Te13, bearing various substituents (Scheme 2B). Expectedly, simple diphenyl tellurether Te8 featured degraded catalytic activity (3aa, 55% after 3 h), although this still represents a
  • significantly superior result compared to catalyst-free conditions (3aa, 22% after 3 h). Electron π-donating substituents considerably improved catalytic activity, with an optimum among tested structures for Te10 (3aa, 74% after 3 h), which is intriguingly similar to the previously reported best catalyst for
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Published 04 Jun 2024

Synthesis and physical properties of tunable aryl alkyl ionic liquids based on 1-aryl-4,5-dimethylimidazolium cations

  • Stefan Fritsch and
  • Thomas Strassner

Beilstein J. Org. Chem. 2024, 20, 1278–1285, doi:10.3762/bjoc.20.110

Graphical Abstract
  • -donating substituents in different positions of the phenyl ring and the bis(trifluoromethylsulfonyl)imide (NTf2) anion. We investigated the effect of additional methyl groups in the backbone of the imidazolium core on the physical properties regarding viscosity, conductivity and electrochemical window
  • investigate the impact on the properties of ILs. The negative impact on viscosity and conductivity due to the higher mass should be comparatively low. We investigated different substituents with electron-donating as well as electron-withdrawing properties at the aryl ring and the difference between the ortho
  • shows the influence of the electronegative fluorine atoms on the electrostatic potential of the cation. Conclusion Based on the synthesis of nine different 1-aryl-4,5-dimethyl substituted imidazoles we report a new class of ionic liquids with electron-donating and -withdrawing substituents, three
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Published 31 May 2024

Synthesis of indano[60]fullerene thioketone and its application in organic solar cells

  • Yong-Chang Zhai,
  • Shimon Oiwa,
  • Shinobu Aoyagi,
  • Shohei Ohno,
  • Tsubasa Mikie,
  • Jun-Zhuo Wang,
  • Hirofumi Amada,
  • Koki Yamanaka,
  • Kazuhira Miwa,
  • Naoyuki Imai,
  • Takeshi Igarashi,
  • Itaru Osaka and
  • Yutaka Matsuo

Beilstein J. Org. Chem. 2024, 20, 1270–1277, doi:10.3762/bjoc.20.109

Graphical Abstract
  • converted to indano[60]fullerene thioketone (FIDS) in high yield by using Lawesson's reagent. Three compounds with different substituents in para position were successfully converted to the corresponding thioketones, showing that the reaction tolerates compounds with electron-donating and electron
  • -withdrawing substituents. Computational studies with density functional theory revealed the unique vibrations of the thioketone group in FIDS. The molecular structure of FIDS was confirmed by single-crystal X-ray analysis. Bulk heterojunction organic solar cells using three evaporable fullerene derivatives
  • . Additionally, the ketone structure acts as a Lewis base, resulting in a passivation effect on Pb2+ [19]. In this study, we designed and synthesized indano[60]fullerene thioketones (FIDSs) with various para-substituents. The vacuum-deposition performance and thermal stability of FIDS were assessed by both
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Published 31 May 2024

Domino reactions of chromones with activated carbonyl compounds

  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 1256–1269, doi:10.3762/bjoc.20.108

Graphical Abstract
  • product. The reaction proved to be rather general and various dienes and chromones were successfully employed to give the corresponding benzozocoumarines in good yields. The yields were in most of the cases in the range of 42 to 65% (over two steps) and did not depend much on the substituents attached to
  • cyclization can be explained by the higher electrophilicity of the aldehyde as compared to the ketone. The yields were in general quite good (51–65%). Relatively low yields (51–52%) were obtained for chromones containing methyl substituents, presumably due to the lower electrophilicity of the chromone based
  • and subsequent acid-catalyzed ring-cleavage and Knoevenagel reaction, similar to the formation of products 21 and 22. The products were formed in 54–84% yields. Again, no systematic trend was observed for the yields. Good yields were observed for dienes containing various substituents located at
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Published 29 May 2024

Synthesis and optical properties of bis- and tris-alkynyl-2-trifluoromethylquinolines

  • Stefan Jopp,
  • Franziska Spruner von Mertz,
  • Peter Ehlers,
  • Alexander Villinger and
  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 1246–1255, doi:10.3762/bjoc.20.107

Graphical Abstract
  • steady state absorption and fluorescence spectroscopy which give insights of the influence of the substitution pattern and of the type of substituents on the optical properties. Keywords: alkynes; catalysis; fluorescence; heterocycles; palladium; Introduction Quinoline is a well-known core structure
  • slighter impact on the emission than electron-donating groups [36]. These findings show that by varying the position and the substituents of the alkynyl groups the properties of the products can be tuned effectively. Conclusion Three different brominated 2-trifluoromethylquinolines have been synthesized
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Published 29 May 2024

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

  • Mohd Farhan Ansari,
  • Atul Kumar Maurya,
  • Abhishek Kumar and
  • Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

Graphical Abstract
  • investigated using four different well-defined phosphine substituents-containing Mn complexes with acetophenone and benzyl alcohol as model substrates. Among these, complex Mn1 showed better results with 2 mol % loading and at low base concentration (Cs2CO3; 5 mol %) in tert-amyl alcohol at 140 °C for 22 h
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Published 21 May 2024
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  • phenyl substituents, have been synthesized and shown to adopt non-planar conformations with the ortho-alkyl groups located above and below the most reactive 1,3-carbons of the furan ring. These bulky substituents provide a strong measure of kinetic stabilization. Thus, 1,3-dimesitylisobenzofuran and 1,3
  • . We previously studied substituent effects in acenes and reported that several substituents promote photooxidative resistance in pentacenes [5] and larger acenes including heptacene [6] and nonacene [7]. One or more substituents that promote photooxidative resistance by quenching singlet oxygen could
  • be utilized on isoacenofurans, too. Additionally, the 1,3-carbons of the furan ring in isoacenofurans are highly reactive towards dienophiles, including singlet oxygen. Thus, we believe that the design of large, persistent isoaceneofurans should include multiple substituents that provide
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Published 17 May 2024
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