Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

• Anka Utama Putra,
• Deniz Çakmaz,
• Nurgül Seferoğlu,
• Alberto Barsella and
• Zeynel Seferoğlu

Beilstein J. Org. Chem. 2020, 16, 2282–2296, doi:10.3762/bjoc.16.189

• all dyes were evaluated by thermogravimetric analysis (TGA). The TGA data showed that all dyes were thermally stable up to 250 °C. Keywords: DFT calculations; NLO; pH sensitive dyes; Schiff base; solvent effect; styryl dyes; Introduction Push-pull organic molecules are a class of organic dyes

• synthesized and characterized a series of new push-pull styryl dyes with free amine functionalities and the corresponding Schiff base analogus. The Schiff bases were found to be able to detect hydroxide anions in DMSO and therefore could act as a pH sensor in a fully aqueous environment. The dyes 8–12 showed

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

• Phil M. Pithan,
• Sören Steup and
• Heiko Ihmels

Beilstein J. Org. Chem. 2020, 16, 904–916, doi:10.3762/bjoc.16.82

• +. Keywords: oxazole; oxidation; quinolizinium; spirooxazines; styryl dyes; Introduction Spiropyrans and spirooxazines are exemplary photochromic compounds that have gained great attention in the last decades because they allow to reversibly alter and control the physical and chemical properties of

Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2 + 2] cycloaddition and cycloreversion

• Sarah Kölsch,
• Heiko Ihmels,
• Jochen Mattay,
• Norbert Sewald and
• Brian O. Patrick

Beilstein J. Org. Chem. 2020, 16, 111–124, doi:10.3762/bjoc.16.13

• switching of binding properties [36]. Apparently, styryl-substituted aromatic derivatives could fill this gap because the [2 + 2] photocyclization reaction of stilbenes and derivatives thereof is a well-established reversible photoreaction [37][38][39][40][41][42][43][44][45][46], and styryl dyes, in

• particular cationic ones, were shown to be efficient DNA binders [47][48][49][50][51][52][53][54][55][56][57][58]. Nevertheless, the photochromic nature of DNA-binding styryl dyes has not been applied to use them as photoswitchable DNA binders. Although, there is one reported example that demonstrates the

Identification of optimal fluorescent probes for G-quadruplex nucleic acids through systematic exploration of mono- and distyryl dye libraries

• Xiao Xie,
• Michela Zuffo,
• Marie-Paule Teulade-Fichou and
• Anton Granzhan

Beilstein J. Org. Chem. 2019, 15, 1872–1889, doi:10.3762/bjoc.15.183

• common feature of mono- and distyryl dyes, including long-known mono-styryl dyes used as mitochondrial probes or protein stains. However, the magnitude of the G4-induced “light-up” effect varies drastically, as a function of both the molecular structure of the dyes and the nature or topology of G4

• rapid topological classification of G4-DNA structures. Keywords: fluorescent probes; G-quadruplex DNA; G-quadruplex RNA; nucleic acids; styryl dyes; Introduction Development of fluorescent probes for G-quadruplex (G4) DNA and RNA is an active research area. In fact, these non-canonical nucleic acid

• and quantum yield, low background fluorescence) are still poorly understood, mostly due to the lack of comparative studies. To explore this aspect, we report the synthesis and systematic study of a library of 61 di- and mono-styryl dyes, as potential “light-up” probes for G4 structures. The study aims

Precious metal-free molecular machines for solar thermal energy storage

• Meglena I. Kandinska,
• Snejana M. Kitova,
• Vladimira S. Videva,
• Stanimir S. Stoyanov,
• Stanislava B. Yordanova,
• Stanislav B. Baluschev,
• Silvia E. Angelova and
• Aleksey A. Vasilev

Beilstein J. Org. Chem. 2019, 15, 1096–1106, doi:10.3762/bjoc.15.106

• Abstract Four benzothiazolium crown ether-containing styryl dyes were prepared through an optimized synthetic procedure. Two of the dyes (4b and 4d) having substituents in the 5-position of the benzothiazole ring are newly synthesized compounds. They demonstrated a higher degree of trans–cis

• -crown-5 ether; benzothiazolium crown ether-containing styryl dyes; E/Z photoisomerization; molecular solar thermal system; Introduction Molecular photoswitches permanently attract considerable interest because they hold potential for application in molecular electronic and photonic devices [1][2][3][4

• improvements and brings the scientists nearer to the identification of the “perfect” MOST system. In this connection we identified crown ether-containing styryl dyes [14][15] as promising substances due to their ability to undergo trans-to-cis photoisomerization (E/Z) with very high quantum yields. In addition

A postsynthetically 2’-“clickable” uridine with arabino configuration and its application for fluorescent labeling and imaging of DNA

• Heidi-Kristin Walter,
• Bettina Olshausen,
• Ute Schepers and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2017, 13, 127–137, doi:10.3762/bjoc.13.16

• by blue and green emitting cyanine-styryl dyes were improved due to the arabino-configured anchor. These oligonucleotides were used as energy transfer donors in hybrids with oligonucleotides modified with acceptor dyes that emit in the yellow-red range. These combinations give energy transfer pairs

• developed and synthesized the 2’-propargyl-modified arabino-configured uridine analog 2, incorporated it into DNA by automated phosphoramidite chemistry, “clicked” it to a variety of our recently established, photostable cyanine-styryl dyes and probed the fluorescence and energy transfer properties by

• corresponding unmodified counterstrand. The four fluorophores D1 [23], a blue emitter excitable at 389 nm, D2 [24], D3 [19], and D4 [24], all green emitters excitable at 450–460 nm, that were “clicked” to the oligonucleotides DNA1a and DNA1r belong to our recently established class of cyanine-styryl dyes that