Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• of prospective applications of indigo photoswitches. Keywords: indigoid dyes; photochemistry; photophysics; photoswitching; E–Z isomerization; Review Historical milestones in the development of photochromic indigo derivatives 1954: first reported photochromic indigo derivative – N,N'-diacetylindigo

Photoinduced in situ generation of DNA-targeting ligands: DNA-binding and DNA-photodamaging properties of benzo[c]quinolizinium ions

• Julika Schlosser,
• Olga Fedorova,
• Yuri Fedorov and
• Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 101–117, doi:10.3762/bjoc.20.11

• -Mix 11118 (Fisher Bioblock Scientific). E-Pure water was obtained with an ultrapure water system D 4632-33 (Wilhelm Werner GmbH, Leverkusen, Germany) with filters D 0835, D 0803, and D 5027 (2×). CD- and LD-spectroscopic measurements were performed on a Chirascan spectrometer (Applied Photophysics

Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals

• Alessandro L. Alves,
• Simone V. Bernardino,
• Carlos H. Stadtlober,
• Edivandro Girotto,
• Giliandro Farias,
• Rodney M. do Nascimento,
• Sergio F. Curcio,
• Thiago Cazati,
• Marta E. R. Dotto,
• Juliana Eccher,
• Leonardo N. Furini,
• Hugo Gallardo,
• Harald Bock and
• Ivan H. Bechtold

Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128

• columnar hexagonal mesophase stable at room temperature, and compound 2 is pyrene-based crystalline with columnar rectangular order preserved at room temperature. Photoluminescence lifetime measurements indicated that molecular aggregation and π-stacking interactions dominate the photophysics of films

The effect of dark states on the intersystem crossing and thermally activated delayed fluorescence of naphthalimide-phenothiazine dyads

• Liyuan Cao,
• Xi Liu,
• Xue Zhang,
• Jianzhang Zhao,
• Fabiao Yu and
• Yan Wan

Beilstein J. Org. Chem. 2023, 19, 1028–1046, doi:10.3762/bjoc.19.79

• states. Femtosecond transient absorption spectroscopy (fs-TA) was rarely used for the study of the photophysics of the TADF emitters [12][34][35][36][37], since it suffers from the limitation of the time window of detection (up to a few ns). On the other hand, nanosecond transient absorption spectroscopy

• electron donor for the construction of electron donor–acceptor TADF molecules is carbazole. However, since our aim was to study the TADF photophysics with model TADF emitters, the use of phenothiazine (PTZ) instead of carbazole presents a few advantages. First, upon connection of the electron acceptor (i.e

Sinensiols H–J, three new lignan derivatives from Selaginella sinensis (Desv.) Spring

• Qinfeng Zhu,
• Beibei Gao,
• Qian Chen,
• Tiantian Luo,
• Guobo Xu and
• Shanggao Liao

Beilstein J. Org. Chem. 2022, 18, 1410–1415, doi:10.3762/bjoc.18.146

• Chirascan-plus CD spectrometer (Applied Photophysics Ltd., UK). NMR spectral data were measured on a Bruker DRX-600 spectrometer. Silica gel (200–300 mesh, Qingdao Haiyang Chemical Co. Ltd., China) was used for column chromatography. Semi-preparative HPLC was performed on an Agilent 1260 liquid

A Streptomyces P450 enzyme dimerizes isoflavones from plants

• Run-Zhou Liu,
• Shanchong Chen and
• Lihan Zhang

Beilstein J. Org. Chem. 2022, 18, 1107–1115, doi:10.3762/bjoc.18.113

• acquired under N2 gas by a Chirascan V100 spectrometer (Applied Photophysics). Strain cultivation was performed at 28 °C in an incubator for agar plates or in a rotary shaker at 200 rpm for liquid media. Strain preparation and fermentation The strain S. cattleya NRRL 8057 was purchased from the China

Comparative study of thermally activated delayed fluorescent properties of donor–acceptor and donor–acceptor–donor architectures based on phenoxazine and dibenzo[a,j]phenazine

• Saika Izumi,
• Prasannamani Govindharaj,
• Anna Drewniak,
• Paola Zimmermann Crocomo,
• Satoshi Minakata,
• Leonardo Evaristo de Sousa,
• Piotr de Silva,
• Przemyslaw Data and
• Youhei Takeda

Beilstein J. Org. Chem. 2022, 18, 459–468, doi:10.3762/bjoc.18.48

• . The photophysics of both molecules was analyzed using a unified approach for photophysical rate calculations that employs the nuclear ensemble method as implemented in the NEMO software [21][22] interfaced with the QChem 5.0 program suite [23]. A total of 500 geometries were sampled for each molecule

Chemical syntheses and salient features of azulene-containing homo- and copolymers

• Vijayendra S. Shetti

Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139

• , anti-Kasha photophysics, and a small HOMO–LUMO gap when compared to its isomer, naphthalene. These properties make azulene-containing polymers an intriguing entity in the field of functional polymers, especially for organic electronic applications like organic field-effect transistors (OFET) and

Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties

• Peter Jonas Wickhorst,
• Mathilda Blachnik,
• Denisa Lagumdzija and
• Heiko Ihmels

Beilstein J. Org. Chem. 2021, 17, 991–1000, doi:10.3762/bjoc.17.81

• dichroism (LD): Chirascan CD spectrometer, Applied Photophysics. Flow-LD: High Shear Cuvette Cell Accessory (Applied Photophysics); the LD samples were recorded in a rotating cuvette with a shear gradient of 1200 s−1. Melting points: Büchi 545 (Büchi, Flawil, CH). Materials Berberrubine (1b) was synthesized

Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives

• Jonas Becher,
• Daria V. Berdnikova,
• Heiko Ihmels and
• Christopher Stremmel

Beilstein J. Org. Chem. 2020, 16, 2795–2806, doi:10.3762/bjoc.16.230

• spectrometer at 20 °C. CD-spectroscopic measurements were performed with a Chirascan spectrometer (Applied Photophysics) in quartz cells (1.0 mm). Melting points were measured with a Büchi 545 (Büchi, Flawil, CH) and are uncorrected. Materials Commercially available reagents and reactants were used without

Recent developments in enantioselective photocatalysis

• Callum Prentice,
• James Morrisson,
• Andrew D. Smith and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

• Bernd Strehmel,
• Christian Schmitz,
• Ceren Kütahya,
• Yulian Pang,
• Anke Drewitz and
• Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

• differ. It facilitates their use with modern light sources such LEDs and lasers with emission in the NIR between 800–1100 nm. A purposeful use requires a more detailed understanding of the photochemistry occurring in such compounds. Photophysics and photochemistry General aspects Figure 1 depicts

• photochemistry and photophysics of NIR absorbers from the simplest point of view. Excitation based on one-photon excitation (OP) results in population of higher vibrational levels of the first excited singlet state (S1), which fast relax by vibrational relaxation into the lowest vibrational level of the S1. The

Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

• Natascha Breuer,
• Irina Gruber,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 2684–2703, doi:10.3762/bjoc.15.262

• prerequisites for the application of fluorescent substances in chemistry, medicine and materials science [1]. With this respect emissive small molecules [2], fluorescent proteins [3], and quantum dots have received considerable attention and remarkable progress in their synthesis and photophysics has been

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

• systemic delivery; “super”-quenching minimizes the imaging background and phototoxicity to normal tissues [27]. The complexation of GC5A with ICT dyes 1,8-ANS and 2,6-TNS are considered involving ICT processes in their photophysics [40][41] because of their intramolecular electron-donating and electron

• excited-state photophysics, redox behavior and utilizable luminescence properties [60][61]. These Ru complexes exhibit transitions involving charge transfer from the metal-centered d orbital to the ligand p orbital, commonly known as metal-to-ligand charge transfer (MLCT). Upon excitation, the excited

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

• phosphorescent molecules, e.g., in the microsecond time scale [69]. Due to these really interesting properties, metal-based and metal-free TADF fluorescent materials have been extensively studied over the past few years, improving the photophysics of this new class of materials by molecular design [72][73][74

Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

• Amrita Das,
• Mitasree Maity,
• Simon Malcherek,
• Burkhard König and
• Julia Rehbein

Beilstein J. Org. Chem. 2018, 14, 2520–2528, doi:10.3762/bjoc.14.228

• ps/div, 10 ns/div, 10µs/div; tmax = 3.5 µs to 10 µs) provided information on photophysics and photochemistry of the single reactants. Figure 4 shows the strong luminescence of the catalyst (red line) that overlaps with the transient absorption of the postulated 1,3,5-TMB•+ in the 2-component mixture

Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril

• Mohammad A. Alnajjar,
• Jürgen Bartelmeß,
• Robert Hein,
• Pichandi Ashokkumar,
• Mohamed Nilam,
• Werner M. Nau,
• Knut Rurack and
• Andreas Hennig

Beilstein J. Org. Chem. 2018, 14, 1961–1971, doi:10.3762/bjoc.14.171

• the carbonyl-fringed CB7 rim and the fluorine atoms in the tetrafluoroaniline, which are slightly larger than the hydrogen atoms [57]. The data obtained with 3 could not be fitted satisfactorily, which is presumably due to the more complex photophysics of this dye (see above) and the exchange of 5 was

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

Two novel blue phosphorescent host materials containing phenothiazine-5,5-dioxide structure derivatives

• Feng-Ming Xie,
• Qingdong Ou,
• Qiang Zhang,
• Jiang-Kun Zhang,
• Guo-Liang Dai,
• Xin Zhao and
• Huai-Xin Wei

Beilstein J. Org. Chem. 2018, 14, 869–874, doi:10.3762/bjoc.14.73

• intermolecular forces of molecules. The high thermal values ensure high thermostability and that the amorphous structure can form homogeneous and stable films by vacuum deposition to improve the lifetime of the PhOLEDs. The photophysics, electrochemical and thermal properties of CEPDO and CBPDO are summarized in

• ). Cyclic voltammograms for CEPDO and CBPDO in DCM solution. DSC and TGA curves of CEPDO and CBPDO. Synthetic routes of CEPDO and CBPDO. Photophysics, electrochemical and thermal properties of CEPDO and CBPDO. Supporting Information Supporting Information File 14: Experimental part and copies of NMR

Fluorescent nucleobase analogues for base–base FRET in nucleic acids: synthesis, photophysics and applications

• Mattias Bood,
• Sangamesh Sarangamath,
• Moa S. Wranne,
• Morten Grøtli and
• L. Marcus Wilhelmsson

Beilstein J. Org. Chem. 2018, 14, 114–129, doi:10.3762/bjoc.14.7

Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides

• Li Yang,
• Ping Wu,
• Jinghua Xue,
• Huitong Tan,
• Zheng Zhang and
• Xiaoyi Wei

Beilstein J. Org. Chem. 2017, 13, 1039–1049, doi:10.3762/bjoc.13.103

• state, arising from the chiral nature of molecules. Experimental General experimental procedures Optical rotations were recorded in MeOH on a Perkin-Elmer 343 spectropolarimeter. UV spectra and ECD spectra were obtained simultaneously on a Chirascan CD spectrometer (Applied Photophysics Ltd., England

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

• Ze’en Xiao,
• Senhua Chen,
• Runlin Cai,
• Shao’e Lin,
• Kui Hong and
• Zhigang She

Beilstein J. Org. Chem. 2016, 12, 2077–2085, doi:10.3762/bjoc.12.196

• CDCl3) and coupling constants (J) are given in Hz. ECD spectra were measured on a Chirascan CD spectrometer (Applied Photophysics, London, UK). Single-crystal data were collected on an Agilent Gemini Ultra diffractometer (CuKα radiation). Silica gel (200–300 mesh, Qingdao Marine Chemical Factory) and

From steroids to aqueous supramolecular chemistry: an autobiographical career review

• Bruce C. Gibb

Beilstein J. Org. Chem. 2016, 12, 684–701, doi:10.3762/bjoc.12.69

• using “Click” chemistry [37]. Forming stable complexes for a broad range of guests, the capsules formed by octa-acid are ideal nano-scale (yocto-liter) reaction vessels. Our first foray into this topic relied on collaboration with Vaidhyanathan Ramamurthy, and examined a wide range of photophysics, and

A comparative study of the interactions of cationic hetarenes with quadruplex-DNA forming oligonucleotide sequences of the insulin-linked polymorphic region (ILPR)

• Darinka Dzubiel,
• Heiko Ihmels,
• Mohamed M. A. Mahmoud and
• Laura Thomas

Beilstein J. Org. Chem. 2014, 10, 2963–2974, doi:10.3762/bjoc.10.314

• , Applied Photophysics. Methods All photometric and fluorimetric titrations were performed in thermostated quartz cuvettes at 20 °C. Titrant solutions were freshly prepared by dilution from the stock solution. Spectrophotometer slit widths were 2 nm for photometric experiments and 5 nm for fluorimetric

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

• Bradley D. Rose,
• Peter J. Santa Maria,
• Aaron G. Fix,
• Chris L. Vonnegut,
• Lev N. Zakharov,
• Sean R. Parkin and
• Michael M. Haley

Beilstein J. Org. Chem. 2014, 10, 2122–2130, doi:10.3762/bjoc.10.219

• an Emmanuil Troyanski Fellowship as well as the NSF for a GK-12 Fellowship (DGE-0742540). P.J.S.M. acknowledges the NSF for an REU Summer Fellowship (CHE-1062512). We thank Dr. Johannes Gierschner for initial discussions regarding the photophysics of the IF-6,12-diones as well as Prof. John Anthony