Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

• Shakeel Alvi Rashid Ali Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, Okhla, New Delhi-110025, India 10.3762/bjoc.20.186 Abstract For the first time, herein, we report the synthetic part of the truxene-centred mono-, di- and tri-substituted dipyromethanes (DPMs) in good yields (60

• purified through silica-gel column chromatography. After successfully synthesizing these easy-to-make yet interesting molecules, they were fully characterized by means of the standard spectroscopic techniques (1H NMR, 13C NMR and HRMS). We are of the opinion that these truxene-based systems will be useful

• for diverse applications in future studies. Keywords: condensation; co-timerization; dipyrromethane; Friedel–Crafts acylation; heterocycles; pyrrole; truxene; Introduction The scaffold of truxene (10,15‐dihydro‐5H‐diindeno[1,2‐a;1′,2′‐c]fluorene) and its congeners comprises three fluorene subunits

Design, synthesis and photophysical properties of novel star-shaped truxene-based heterocycles utilizing ring-closing metathesis, Clauson–Kaas, Van Leusen and Ullmann-type reactions as key tools

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2021, 17, 1374–1384, doi:10.3762/bjoc.17.96

• interdisciplinary interest from both fundamental as well as applied viewpoint on account of their wonderful optoelectronic properties. The scientific interest in two-dimensional star-shaped PAHs particularly in truxene architectures arises because of their high thermal stability, exceptional solubility and ease

• with which they can be constructed and modified. Therefore, bearing in mind a wide range of applications of truxene and its congeners, herein we reveal three novel distinctly different routes for the generation of C3-symmetric pyrrole-based truxene architectures by means of cyclotrimerization, ring

• -closing metathesis (RCM), Clauson–Kaas and Ullmann-type coupling reactions as key steps. Moreover, we have also assembled some other interesting heterocyclic systems possessing oxazole, imidazole, benzimidazole, and benzoxazole in the framework of truxene. Additionally, the preliminary photophysical

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

• Aude-Héloise Bonardi,
• Frédéric Dumur,
• Guillaume Noirbent,
• Jacques Lalevée and
• Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

• detailed in Table 9. In order to be concise, only three kinds of organophotocatalysts have been described in the present review. However, over the years, a large number of different organophotocalysts has been described in the literature. Notably, pyrene [89], truxene [90][91][92], polyaromatic

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

• Sambasivarao Kotha,
• Milind Meshram and
• Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

• 40 was subjected to SM coupling in the presence of phenylboronic acid (36) to generate the new spirofluorene 41 (88%, Scheme 6). Interestingly, highly substituted truxene derivatives 45–49 were also synthesized by applying the RCM and SM coupling protocol (Scheme 7). Heterocycles Couture and co

• substituted spirocycles via RCM and SM sequence. Synthesis of highly functionalized bis-spirocyclic derivative 37. Synthesis of spirofluorene derivatives via RCM and SM coupling sequence. Synthesis of truxene derivatives via RCM and SM coupling. Synthesis of substituted isoquinoline derivative via SM and RCM

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• ]. The three TTF units with chiral citronellyl and dihydrocitronellyl chains led to helical one-dimensional stacks in solution to produce fibers that have morphologies depending on the nature of the chiral alkyl group, although an achiral counterpart showed no helicity. C3-symmetric truxene-TTFs 7a–c

Synthesis and properties of novel star-shaped oligofluorene conjugated systems with BODIPY cores

• Clara Orofino-Pena,
• Diego Cortizo-Lacalle,
• Joseph Cameron,
• Muhammad T. Sajjad,
• Pavlos P. Manousiadis,
• Neil J. Findlay,
• Alexander L. Kanibolotsky,
• Dimali Amarasinghe,
• Peter J. Skabara,
• Tell Tuttle,
• Graham A. Turnbull and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2704–2714, doi:10.3762/bjoc.10.285

• structures [17]. A multidimensional molecular architecture provides excellent film-forming properties of the materials and an isotropic morphology of the final film. In the case of oligofluorenes with benzene [18] and truxene cores [19][20][21][22], this design methodology has yielded promising materials for

• ], subporphyrin [26] and truxene [27][28] cores via its meso-position by a phenylethynyl linkage, to the best of our knowledge there is no report on the synthesis of oligofluorene star-shaped systems with BODIPY as a core. The latter would provide extended conjugation not only through the β-position but via the

Metal and metal-free photocatalysts: mechanistic approach and application as photoinitiators of photopolymerization

• Jacques Lalevée,
• Sofia Telitel,
• Pu Xiao,
• Marc Lepeltier,
• Frédéric Dumur,
• Fabrice Morlet-Savary,
• Didier Gigmes and
• Jean-Pierre Fouassier

Beilstein J. Org. Chem. 2014, 10, 863–876, doi:10.3762/bjoc.10.83

• (that usually operates through a reductive cycle; see below) works according to an oxidative cycle (Scheme 10). This is the case when the PIC stands for a truxene-acridinedione derivative Tr-AD (this is one of the possible examples for Scheme 2) [63]. For these PICs, the interaction of the excited

Incorporation of perfluorohexyl-functionalised thiophenes into oligofluorene-truxenes: synthesis and physical properties

• Neil Thomson,
• Alexander L. Kanibolotsky,
• Joseph Cameron,
• Tell Tuttle,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2013, 9, 1243–1251, doi:10.3762/bjoc.9.141

• ; star-shaped molecules; synthesis; truxene; Introduction Star-shaped oligomers share a common central unit with multiple arms branching from the core [1]. The morphology and electronic properties of these oligomers often vary from the linear versions of the arms alone. 10,15-Dihydro-5H-diindeno[1,2-a;1

• ′,2′-c]fluorene, also known as truxene (Figure 1), is a heptacyclic polyarene with C3 symmetry that can be envisaged as three fluorenes that are superimposed through a common central benzene ring [2][3]. Truxene has been used as a starting compound, or a core unit, for larger star-shaped polyarenes

• of the perfluoroalkyl thiophene substituent than those of T1-4FTh. Labelled truxene and compounds T1 and T4. Normalised absorbance (solid) and emission (dashed) of materials in solution (dichloromethane). HOMO−1 (bottom, left), HOMO (bottom, right), LUMO (top, left) and LUMO+1 (top, right) of T1-3FTh

New core-pyrene π structure organophotocatalysts usable as highly efficient photoinitiators

• Sofia Telitel,
• Frédéric Dumur,
• Thomas Faury,
• Bernadette Graff,
• Mohamad-Ali Tehfe,
• Didier Gigmes,
• Jean-Pierre Fouassier and
• Jacques Lalevée

Beilstein J. Org. Chem. 2013, 9, 877–890, doi:10.3762/bjoc.9.101

• architectures (Scheme 2) [42][43][44] are linked PI–PI units (e.g., PI = pyrene) or PI-PI’ (e.g., PI = pyrene and PI’ = 2,2’-dimethoxy-2-phenylacetophenone) and PI moieties (e.g., PI = benzophenone, thioxanthone, 2,2’-dimethoxy-2-phenylacetophenone, pyrene) linked to a trifunctional core (truxene, triazine

• , benzene); the same could be expected by using a difunctional core. In the present paper, we consider a series of eleven di- and trifunctional core-pyrene π compounds Co_Py, where the pyrene moiety is used as a PI. The cores include a functionalized truxene (Py_5), several substituted phenyl rings (Py_2