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

• determined to be 2 and 58 ps, respectively. The observed longer lifetimes attributed to DEA substitution could be due to the larger distance and the Marcus inverted region [143] character, compared with the results obtained for OEF substitution. Guldi et al. synthesized zinc phthalocyanine (ZnPC) covalently

Recent advances in the application of isoindigo derivatives in materials chemistry

• Andrei V. Bogdanov and
• Vladimir F. Mironov

Beilstein J. Org. Chem. 2021, 17, 1533–1564, doi:10.3762/bjoc.17.111

• also found that a device based on compound 45 (R = 2-decyltetradecyl) with the addition of iron phthalocyanine showed slightly better mobility. Liu et al. explain this effect by an improvement in the hole-type conductivity and a tight and even packing of the composite in a thin film [80]. At the same

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

• Yu-Ying Wang,
• Yong Kong,
• Zhe Zheng,
• Wen-Chao Geng,
• Zi-Yi Zhao,
• Hongwei Sun and
• Dong-Sheng Guo

Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139

• luminescent dyes. Fluorescein, eosin Y, rose bengal, tetraphenylporphine sulfonate and sulfonated aluminum phthalocyanine were employed as classical aggregation-induced quenching dyes. 2-(p-Toluidinyl)naphthalene-6-sulfonic acid and 1-anilinonaphthalene-8-sulfonic acid were selected as representatives of

• (EY), rose bengal (RB), tetraphenylporphine sulfonate (TPPS), sulfonated aluminum phthalocyanine (AlPcS4), 2-(p-toluidinyl)naphthalene-6-sulfonic acid (2,6-TNS), 1-anilinonaphthalene-8-sulfonic acid (1,8-ANS), phosphated tetraphenylethylene (P-TPE), sulfonated acedan (TPS), and a ruthenium(II) complex

Synthesis of dipolar molecular rotors as linkers for metal-organic frameworks

• Sebastian Hamer,
• Fynn Röhricht,
• Marius Jakoby,
• Ian A. Howard,
• Xianghui Zhang,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1331–1338, doi:10.3762/bjoc.15.132

• Sonogashira reactions [53]. In the reported procedure, a bulky substituted acetylene derivative was used, probably supressing the formation of the phthalocyanine byproduct to some extent. Indeed, 5,6-dicyano-4,7-bis-(2-trimethylsilylethynyl)-2,1,3-benzothiadiazole (12a) could be synthesized by Sonogashira

• coupling in a low yield of 10% alongside with phthalocyanine byproducts. The triisopropylsilyl-protected derivative 12b could be obtained in a slightly higher yield of 21%, presumably due to the bulkier TIPS-groups. A crystal structure of this compound was obtained (see Supporting Information File 2). To

• increase the yield and avoid these side reactions, we reacted diiodo compound 11b with 1-trimethylsilyl-2-tributylstannylacetylene in a Stille cross coupling, where no formation of phthalocyanine or similar side products was observed. Changing the catalyst from tetrakis(triphenylphosphine)palladium(0) to

Synthesis and spectroscopic properties of β-meso directly linked porphyrin–corrole hybrid compounds

• Baris Temelli and
• Hilal Kalkan

Beilstein J. Org. Chem. 2018, 14, 187–193, doi:10.3762/bjoc.14.13

• obtaining multiporphyrin arrays [7][8][9] that could stabilize only metal ions in a bivalent state. To overcome this limitation, porphyrin conjugates with different chromophore groups such as fullerene [10][11][12], BODIPY [13][14][15], corrole [16][17][18][19][20][21][22][23], phthalocyanine [24][25][26

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• by the strong electronegativity of fluorine. Therefore, it is expected that trifluoroethoxy-substituted phthalocyanines can be applied to new industrial fields. This review summarizes the synthesis and application of trifluoroethoxy-substituted phthalocyanine and subphthalocyanine derivatives

• . Keywords: aggregation; fluorine; phthalocyanine; subphthalocyanine; trifluoroethoxy; Introduction Phthalocyanines [1][2][3] are analogues of porphyrin condensed with four isoindoline units via a nitrogen atom and exhibit a deep blue color due to their wide 18π electron conjugation. Among them, the most

• fundamental phthalocyanine copper complex, which does not have a substituent on its periphery, is known as a blue organic pigment called phthalocyanine blue [4][5][6][7]. Phthalocyanines have long been used as a blue pigment for, e.g., road signs and bullet trains because they can be manufactured cheaply, are

Superstructures with cyclodextrins: Chemistry and applications IV

• Gerhard Wenz

Beilstein J. Org. Chem. 2017, 13, 2157–2159, doi:10.3762/bjoc.13.215

• nanoparticles with the sensitizer Zn-phthalocyanine and the antineoplastic drug docetaxel. These materials might be applicable for dual cancer therapy [15]. Another self-assembled CD nanocarrier for the photoreactive dye squaraine that is useful for photodynamic therapy is described in this Thematic Series [16

A self-assembled cyclodextrin nanocarrier for photoreactive squaraine

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248

• scattering and absorption by tissue is minimized and a more in-depth therapy becomes possible. The search for more effective compounds with absorption in the near infrared includes amongst others cyanine [10], bodipy [11], and phthalocyanine [12] photosensitizers and has lately led to the consideration of a

• applications when a well-known PS, phthalocyanine, was used to decorate the cyclodextrin vesicles [37][38]. The immobilization led to an increased photoactivity of the phthalocyanines due to suppression of aggregation and inactivation of the PS at the surface of the CDVs. In this contribution we show that

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

• Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

• -aminophosphonates. Unfortunately there are only a few examples of Kabachnik–Fields reactions of heterocycloalkanones in the literature. The tetra(tert-butyl)phthalocyanine–AlCl complex catalyzed three component reaction of N-Boc-piperidin-4-one (23) with (EtO)2P(O)H (24) and benzylamine (25) afforded the cyclic α

• the synthesis of α-aminophosphonates. Phthalocyanine–AlCl catalyzed Kabachnik–Fields reaction of N-Boc-piperidin-4-one with diethyl phosphite and benzylamine. Kabachnik–Fields reaction of isatin with diethyl phosphite and benzylamine. Magnetic Fe3O4 nanoparticle-supported phosphotungstic acid

Iron complexes of tetramine ligands catalyse allylic hydroxyamination via a nitroso–ene mechanism

• David Porter,
• Belinda M.-L. Poon and
• Peter J. Rutledge

Beilstein J. Org. Chem. 2015, 11, 2549–2556, doi:10.3762/bjoc.11.275

• only the allylic amination product was formed [36][38]. Conversely Jørgensen and Johannsen report that N-phenylhydroxylamine and 1,3-cyclohexadiene in the presence of iron(II) phthalocyanine do form the Diels–Alder cycloadduct [35]. Although the outcomes with the different catalysts were contrasting

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

• examples [30][31][32][33]. Other functional units such as fullerenes [34][35], cyclodextrins [36], porphyrin [37], and phthalocyanine [38][39][40] can also be introduced into the core of radial oligo-TTFs. As shown in Figure 1, TTF-annelated porphyrin 1 was synthesized by Becher and co-workers in 2001 [37

• ]. Reflecting its strong π-donor ability, 1 was oxidized spontaneously in solution to afford 1•+ under ambient conditions. Multifunctional TTF-crown ether-substituted phthalocyanine (Pc) 2a and its copper(II) complex 2b were reported by Amabilino, Rowan, Nolte, and co-workers in 2005 [40]. The giant molecule 2a

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

• Igor B. Krylov,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

• -immobilized manganese phthalocyanine/H2O2aq [166], a Ni(II) complex/H2O2aq [167], and ZnBr2/H2O2 [168]. The oxidative C–O coupling of aromatic aldehydes 181 with cycloalkanes 182 was accomplished in the presence of the Cu(OAc)2/t-BuOOH system to prepare products 183. This reaction is unusual in that it

Organic synthesis using photoredox catalysis

• Axel G. Griesbeck

Beilstein J. Org. Chem. 2014, 10, 1097–1098, doi:10.3762/bjoc.10.107

• other Ru or Ir complexes) with strong MLCT transitions, organic dyes such as xanthene, porphyrine or phthalocyanine dyes (e.g., eosin Y), and colloidal semiconductor particles (e.g., TiO2) [1][2][3][4][5][6][7][8][9]. In addition, combinations of light-absorbing materials have been studied such as dye

Synthesis, photophysical and electrochemical characterization of terpyridine-functionalized dendritic oligothiophenes and their Ru(II) complexes

• Amaresh Mishra,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2013, 9, 866–876, doi:10.3762/bjoc.9.100

• -functionalization of oligothiophene dendrons with optically and/or redox active perylenebisimide, phthalocyanine and quinoxaline units have been developed as possible light-harvesting molecules [43][44][45]. We report herein the synthesis of oligothienylene-ethynylene based 3-dimensional molecular materials, namely

Improved syntheses of high hole mobility phthalocyanines: A case of steric assistance in the cyclo-oligomerisation of phthalonitriles

• Daniel J. Tate,
• Rémi Anémian,
• Richard J. Bushby,
• Suwat Nanan,
• Stuart L. Warriner and
• and Benjamin J. Whitaker

Beilstein J. Org. Chem. 2012, 8, 120–128, doi:10.3762/bjoc.8.14

• Chemistry, University of Leeds, Woodhouse Lane, Leeds, LS2 9JT, United Kingdom 10.3762/bjoc.8.14 Abstract It has been shown that the base-initiated cyclo-oligomerisation of phthalonitriles is favoured by bulky α-substituents making it possible to obtain the metal-free phthalocyanine directly and in high

• yield. The phthalocyanine with eight α-isoheptyl substituents gives a high time-of-flight hole mobility of 0.14 cm2·V−1·s−1 within the temperature range of the columnar hexagonal phase, that is 169–189 °C. Keywords: high hole mobility; phthalocyanine; steric assistance; Thorpe–Ingold effect; time-of

• 85 °C and 0.20 cm2·V−1·s−1 in the Colh phase at 100 °C) [14][15]. Furthermore, this phthalocyanine gives good time-of-flight electron transits even in an ambient atmosphere [15]. As a result, related α-alkylated phthalocyanines are attracting interest for use in organic devices, such as solar cells

Synthesis of mesogenic phthalocyanine-C₆₀ donor–acceptor dyads designed for molecular heterojunction photovoltaic devices

• Yves Henri Geerts,
• Olivier Debever,
• Claire Amato and
• Sergey Sergeyev

Beilstein J. Org. Chem. 2009, 5, No. 49, doi:10.3762/bjoc.5.49

• /bjoc.5.49 Abstract A series of phthalocyanine-C60 dyads 2a–d was synthesized. Key steps in their synthesis are preparation of the low symmetry phthalocyanine intermediate by the statistical condensation of two phthalonitriles, and the final esterification of the fullerene derivative bearing a free COOH

• example of LC phthalocyanine-C60 dyads. Keywords: donor–acceptor dyad; fullerene; liquid crystals; phthalocyanine; phthalonitrile; Introduction Among sustainable energy technologies, photovoltaic (PV) conversion of solar energy is considered as a promising solution. Although currently the market is

• materials for photovoltaic devices. Within the concept of a “molecular heterojunction”, a number of phthalocyanine-fullerene dyads and triads were synthesized [34][35][36][37][38] and long-lived photoinduced charge transfer was demonstrated in these type of materials [39]. Although examples of mesogenic

Progress in liquid crystal chemistry

• Sabine Laschat

Beilstein J. Org. Chem. 2009, 5, No. 48, doi:10.3762/bjoc.5.48

• diverse topics such as phthalocyanine-fullerene hybrid materials for photovoltaic devices, functional metallomesogens, coaxial electrospinning of liquid crystal-containing microfibers, banana-discotic hybrid systems, ionic liquid crystals, relations between molecular length distribution and formation of