Small anion-assisted electrochemical potential splitting in a new series of bistriarylamine derivatives: organic mixed valency across a urea bridge and zwitterionization

• Keishiro Tahara,
• Tetsufumi Nakakita,
• Alyona A. Starikova,
• Takashi Ikeda,
• Masaaki Abe and
• Jun-ichi Kikuchi

Beilstein J. Org. Chem. 2019, 15, 2277–2286, doi:10.3762/bjoc.15.220

• on evaluating the intervalence charge transfer (IVCT) transition near-infrared (NIR) absorption from NAr3 to NAr3•+ units [1][2][3][4][5]. The IVCT absorptions of MV compounds are generally more pronounced in organic species [19][20] than in their inorganic counterparts. The strong IVCT

Functional panchromatic BODIPY dyes with near-infrared absorption: design, synthesis, characterization and use in dye-sensitized solar cells

• Quentin Huaulmé,
• Cyril Aumaitre,
• Outi Vilhelmiina Kontkanen,
• David Beljonne,
• Alexandra Sutter,
• Gilles Ulrich,
• Renaud Demadrille and
• Nicolas Leclerc

Beilstein J. Org. Chem. 2019, 15, 1758–1768, doi:10.3762/bjoc.15.169

• displaying a panchromatic absorption with an extension to the near-infrared (NIR) range. An innovative synthetic approach for preparing the 2,3,5,6-tetramethyl-BODIPY unit is disclosed, and a versatile way to further functionalize this unit has been developed. The optoelectronic properties of the two dyes

• -dipyrromethene; BODIPY; dye-sensitized solar cells; near-infrared absorbers; organic dyes; Introduction The past two decades have witnessed tremendous efforts to develop alternative photovoltaic (PV) technologies. Among them, dye-sensitized solar cells (DSSCs) display numerous advantages compared to its fully

• of DSSCs, the development of new dye molecules better matching the solar emission spectrum or exhibiting absorption in the near-infrared (NIR) range could be a fruitful strategy. Several families of molecules displaying an infrared absorption have been investigated in the last decade, such as

Reversible end-to-end assembly of selectively functionalized gold nanorods by light-responsive arylazopyrazole–cyclodextrin interaction

• Maximilian Niehues,
• Patricia Tegeder and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2019, 15, 1407–1415, doi:10.3762/bjoc.15.140

• a longitudinal SPR (LSPR) band that can reach up to the near infrared (NIR) region [9]. The LSPR band can be tuned over a wider wavelength range than for isotropic nanoparticles by varying the aspect ratio of the AuNR or by the assembly of multiple AuNR into linear clusters [10]. These linear

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

• opportunity to construct organic luminescent materials and could be engaged in the manufacture of high-performance supramolecular dye lasers [24][48]. The complexation of GC5A with the two-photon fluorescent probe Two-photon excitation microscopy is a fluorescence imaging technique utilizing near-infrared

Molecular recognition using tetralactam macrocycles with parallel aromatic sidewalls

• Dong-Hao Li and
• Bradley D. Smith

Beilstein J. Org. Chem. 2019, 15, 1086–1095, doi:10.3762/bjoc.15.105

• enables them to be effective hosts for a wide range of guest molecules including organic biscarbonyl derivatives, near-infrared dyes, acenes, precious metal halide complexes, trimethylammonium ion-pairs, and saccharides. Keywords: fluorescent dye; host–guest chemistry; hydrogen bonding; hydrophobic

• flexibility of the macrocyclic tetralactams enables them to be effective hosts for a wide range of guest molecules including organic biscarbonyl derivatives, near-infrared dyes, acenes, precious metal halide complexes, trimethylammonium ion pairs, and saccharides. Because of this versatility, macrocyclic

Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions

• Angélica de Fátima S. Barreto and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2019, 15, 906–930, doi:10.3762/bjoc.15.88

• -MiB. Functional macrocycles have been developed with dye-modified and photoswitchable moieties by MiBs [43]. The approach employed the use of bifunctionalized near-infrared (NIR) dyes containing two carboxylic acid moieties with diisocyanide building blocks providing the formation of somewhat flexible

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

• Ayato Yamada,
• Manabu Abe,
• Yoshinobu Nishimura,
• Shoji Ishizaka,
• Masashi Namba,
• Taku Nakashima,
• Kiyofumi Shimoji and
• Noboru Hattori

Beilstein J. Org. Chem. 2019, 15, 863–873, doi:10.3762/bjoc.15.84

• , Japan Department of Molecular and Internal Medicine, Graduate School of Biomedical & Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, Hiroshima 734-8551, Japan 10.3762/bjoc.15.84 Abstract Novel caged nitroxides (nitroxide donors) with near-infrared two-photon (TP) responsive

• photochemical release of nitroxides should be achieved in the presence of O2. Thus, the triplet sensitized method may not be useful for physiological studies. The application of alkoxyamines as theranostic agents [37][38][39][40] has been proposed and reported by Brémond and co-workers [41][42]. Near-infrared

• (Figure 2c,e). The TP photolysis of 2a (10 mM) and 2b (10 mM) was carried out in benzene under atmospheric conditions using 710, 720, 730, 740, 750, and 760 nm near infrared light from a Ti:sapphire laser (pulse width 100 fs, 80 MHz) emitting at an average of 700 mW (Figure 3 for 2a and Supporting

Novel solid-phase strategy for the synthesis of ligand-targeted fluorescent-labelled chelating peptide conjugates as a theranostic tool for cancer

• Sagnik Sengupta,
• Mena Asha Krishnan,
• Premansh Dudhe,
• Ramesh B. Reddy,
• Bishnubasu Giri,
• Sudeshna Chattopadhyay and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2018, 14, 2665–2679, doi:10.3762/bjoc.14.244

• diagnosis and deep tissue imaging of cancers and inflammatory diseases. Near infrared fluorophores containing a free or activated carboxylic group (e.g., IRDye 800CW NHS ester) can also be conjugated with the peptidic spacer using this methodology through amide coupling reaction. Moreover, the bioconjugates

Synthesis and characterization of π–extended “earring” subporphyrins

• Haiyan Guan,
• Mingbo Zhou,
• Bangshao Yin,
• Ling Xu and
• Jianxin Song

Beilstein J. Org. Chem. 2018, 14, 1956–1960, doi:10.3762/bjoc.14.170

• corresponding Pd complexes exhibited remarkably near-infrared absorptions. Based on our previous work, we herein designed a subporphyrin with one “earring”. The different geometry and properties could be envisioned due to the bowl-shaped structure and 14π-electron configuration of subporphyrin. To construct the

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes

• Cristina Cebrián and
• Matteo Mauro

Beilstein J. Org. Chem. 2018, 14, 1459–1481, doi:10.3762/bjoc.14.124

• and blue (RGB) portions of the visible spectrum. In addition, achievement of efficient emission beyond such range towards ultraviolet (UV) and near infrared (NIR) regions was also challenged. By employing TMCs as triplet emitters in OLEDs, remarkably high device performances were demonstrated, with

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

• attention in recent years is the benzene-fused phthalocyanine dimer in which two phthalocyanines are fused together, having a common benzene ring. The benzene-fused dimer shows strong absorption in the near infrared region due to its large conjugated planar π-systems, and exhibits interesting features such

Extrusion – back to the future: Using an established technique to reform automated chemical synthesis

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9

• literature demonstrating the utilisation of near-infrared spectroscopy for online monitoring to determine where in the extruder the cocrystal begins to form. Consequently this also provides feedback regarding screw configuration and deductions can be made as to whether sufficient mechanical energy is being

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

• , which have the disadvantage of an absorption wavelength in the range of visible light [8][9]. Visible light is scattered and absorbed by the inhomogeneous biological tissue. In order to optimise efficiency, it is vital to skew the absorption range of the PS towards the near infrared range. Then, the

• 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

Biradical vs singlet oxygen photogeneration in suprofen–cholesterol systems

• Fabrizio Palumbo,
• Francisco Bosca,
• Isabel M. Morera,
• Inmaculada Andreu and
• Miguel A. Miranda

Beilstein J. Org. Chem. 2016, 12, 1196–1202, doi:10.3762/bjoc.12.115

• singlet oxygen was assessed by time-resolved near infrared emission studies in dichloromethane using perinaphthenone as standard. The quantum yields (ΦΔ) were 0.52 for 1 and 2 and 0.56 for 3. In conclusion, SP-α-Ch dyads are unique in the sense that they can be used to photogenerate both biradicals and

• assess the capability of dyads 1–3 to photosensitize the production of excited singlet molecular oxygen (1O2 or 1Δg), time-resolved near infrared emission studies were carried out in dichloromethane using perinaphthenone (PN) as standard. The formation of this reactive oxygen species was detected by its

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• polymer backbone. Upon oxidation, the film of polymer 37 exhibited a broad ill-defined band extending from 700 nm into the near infrared range. The intensity of the π–π* transition in this case diminished upon oxidation, but this band still remained the most intense feature of the spectrum across the

Glycoluril–tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests

• Yoann Cotelle,
• Marie Hardouin-Lerouge,
• Stéphanie Legoupy,
• Olivier Alévêque,
• Eric Levillain and
• Piétrick Hudhomme

Beilstein J. Org. Chem. 2015, 11, 1023–1036, doi:10.3762/bjoc.11.115

• 825 nm and a broad band in near infrared range beyond 1300 nm (Figure 6). In agreement with the simulated concentration–time profiles in thin layer conditions (Figure 6 – bottom), the appearance of the absorption bands centered around 825 and beyond 1300 nm were attributed to the formation of [(TTF)2

First synthesis of meso-substituted pyrrolo[1,2-a]quinoxalinoporphyrins

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2014, 10, 808–813, doi:10.3762/bjoc.10.76

• ][12][13], organic light emitting diodes [14][15], near infrared dyes [16][17][18], hybrid solar cells [19][20][21][22], and biosensors [23][24][25] due to their intense optical absorptions and photoluminescence characteristics. On the other hand, compounds containing a pyrrolo[1,2-a]quinoxaline

The chemistry of isoindole natural products

• Klaus Speck and
• Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

• yellow 139 (12), which is sold by BASF as Paliotol® Yellow K 1841 belongs to the class of highly resistant and effective 1,3-disubstituted isoindoline dyes. Recently, the use of isoindoles as red to near-infrared fluorophores was reported [12]. Another interesting isoindole-based dye, 25, arises from the

Amyloid-β probes: Review of structure–activity and brain-kinetics relationships

• Todd J. Eckroat,
• Abdelrahman S. Mayhoub and
• Sylvie Garneau-Tsodikova

Beilstein J. Org. Chem. 2013, 9, 1012–1044, doi:10.3762/bjoc.9.116

• relationships with regards to affinity for target and brain kinetics. Several probes discussed herein show particularly promising results and will be of immense value moving forward in the fight against AD. Keywords: Alzheimer’s disease; in vivo detection; near-infrared fluorescence probes; PET/SPECT imaging

• radiolabeled early-diagnostic probes according to their scaffolds, with a special emphasis on their synthesis as well as their structure–activity and brain-kinetics relationships. We also provide a brief summary of the latest developments related to the detection of Aβ plaques by near-infrared fluorescence

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

• 0.15 and 0.24, respectively. Excitation of complexes 1 and 2 at their respective 1MLCT band in deaerated acetonitrile resulted in weak emissions at 693 nm and 755 nm and extended to the near-infrared region. For complexes on the basis of their structureless emission and low fluorescence quantum yields

Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties

• Antonio Avellaneda,
• Courtney A. Hollis,
• Xin He and
• Christopher J. Sumby

Beilstein J. Org. Chem. 2012, 8, 71–80, doi:10.3762/bjoc.8.7

• electron deficient derivatives, 2 and 3, along with the previously synthesised compounds hexa(2-pyridyl)[3]radialene, hexa(3-pyridyl)[3]radialene, and hexakis(4-cyanophenyl)[3]radialene, show a weak absorption in the near infrared (around 800 nm). This is consistent with spectra observed for the radical

Hybrid biofunctional nanostructures as stimuli-responsive catalytic systems

• Gernot U. Marten,
• Thorsten Gelbrich and
• Annette M. Schmidt

Beilstein J. Org. Chem. 2010, 6, 922–931, doi:10.3762/bjoc.6.98

• this respect is the change of temperature. Polymeric materials show a wide range of thermoresponsive effects that can be explored for a discontinuous change of diffusion or reaction rate [1][2][3]. The temperature increase can for example be restricted locally by using near infrared (NIR) irradiation

Conjugated polymers containing diketopyrrolopyrrole units in the main chain

• Bernd Tieke,
• A. Raman Rabindranath,
• Kai Zhang and
• Yu Zhu

Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92

• ; photoluminescence; solar cell; Introduction A useful strategy in the design of new polymers for electronic applications is to incorporate chromophores which are highly absorbing and emitting in the visible and near infrared region into π-conjugated polymers chains. Potentially useful chromophores for electronic

• )DPP] by Yamamoto coupling of a dibrominated thiophenylDPP derivative such as M-3. An ambipolar near-infrared light-emitting transistor (LET) could be prepared from this material which exhibited hole and electron mobilities of 0.1 cm2 V−1 s−1 and up to 0.09 cm2 V−1 s−1, respectively. These values were