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Search for "bathochromic shift" in Full Text gives 108 result(s) in Beilstein Journal of Organic Chemistry.

On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals

  • Daniel Straub,
  • Markus Gross,
  • Mona E. Arnold,
  • Julia Zolg and
  • Alexander J. C. Kuehne

Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80

Graphical Abstract
  • nm for the triaryl oxyether-TTM and λem = 655 nm for the triaryl thioether-TTM (in dichloromethane (DCM)) [44]. The stronger bathochromic shift and the loss of vibrational features in the photoluminescence spectrum point towards a CT excited state in the triaryl thioether-TTM, which could explain the
  • -shaped distribution for ϕ. The bathochromic shift in λem has previously been described to result from the better stabilization of the CT excited state for stronger donors, and therefore a stabilization of the highest occupied molecular orbital (HOMO) when only considering the acceptor moiety (see also
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Published 21 May 2025

Substituent effects in N-acetylated phenylazopyrazole photoswitches

  • Radek Tovtik,
  • Dennis Marzin,
  • Pia Weigel,
  • Stefano Crespi and
  • Nadja A. Simeth

Beilstein J. Org. Chem. 2025, 21, 830–838, doi:10.3762/bjoc.21.66

Graphical Abstract
  • bathochromic shift of the n→π* absorption band further moving their UV–vis absorption spectrum towards the therapeutic window [35]. Moreover, a similar modification in stilbene-based photoswitches and molecular motors showed an increase in performance and photoisomerization quantum yield [36][37]. Consequently
  • * transition, while the weaker n→π* band shows absorption maxima in the range of 410–451 nm in CH3CN. The introduction of methyl and acyl groups on one nitrogen of the pyrazole ring led to a hyperchromic effect and a minor bathochromic shift. Also, the introduction of an EDG or EWG on the R position led to
  • minor hyperchromic effects and a bathochromic shift (exemplary the UV–vis absorption spectra of NAc-PAPs are displayed in Figure 1 and a full set is available in Supporting Information File 1, section 3.5). In the case of EWGs, we observed positive hyperchromic effects while for EDGs negative
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Published 25 Apr 2025

Synthesis and photoinduced switching properties of C7-heteroatom containing push–pull norbornadiene derivatives

  • Daniel Krappmann and
  • Andreas Hirsch

Beilstein J. Org. Chem. 2025, 21, 807–816, doi:10.3762/bjoc.21.64

Graphical Abstract
  • incorporating larger heteroatoms in the bridge moiety, we anticipate a bathochromic shift that would facilitate absorption match with the solar emission spectrum. Results and Discussion Synthesis The library of new heterocyclic NBD molecules synthesized and investigated in this study is presented in Scheme 1
  • . Photoswitching The photoswitching of the NBDs to corresponding QCs was monitored by UV–vis and 1H NMR spectroscopy. With increasing electronegativity of the bridge-atom, a slight bathochromic shift in the absorption spectra of the parent NBD precursors O-NBD1 and N-NBD1 was found (Figure 2a and 2c). For the
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Published 22 Apr 2025

Red light excitation: illuminating photocatalysis in a new spectrum

  • Lucas Fortier,
  • Corentin Lefebvre and
  • Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

Graphical Abstract
  • of lower-energy photons in second- and third-row transition metals compared to their first-row counterparts [13]. These phenomena are specifically improved when potent π-acceptor ligands are used due to their low-energy π* antibonding orbitals resulting in a bathochromic shift of the MLCT absorption
  • to narrow both absorption and emission peaks, along with a bathochromic shift in their spectra. Heptamethin cyanins, in particular, are highly relevant for NIR applications, making them valuable in photochemistry. Additionally, their solubilities, redox and photophysical properties can be fine-tuned
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Published 07 Feb 2025

Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

  • Anastasia I. Ershova,
  • Sergey V. Fedoseev,
  • Konstantin V. Lipin,
  • Mikhail Yu. Ievlev,
  • Oleg E. Nasakin and
  • Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

Graphical Abstract
  • ) in tetrachloromethane (CTC) to 588 nm (orange) in formic acid. Therefore, it was found that compound 1c was characterized by a large Stokes shift upon increasing the solvent polarity, which reached 150 nm (5824 cm−1) in formic acid. This was associated with the bathochromic shift of the emission band
  • maxima of compounds 1a–i were in the range of 402–510 nm (Figure 5, left). The most blue-shifted absorbance was observed for stilbazole 1a, bearing no conjugated donor groups. Depending on their number and donor strength, the introduction of electron-donating substituents led to a bathochromic shift. The
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Published 19 Nov 2024

C–C Coupling in sterically demanding porphyrin environments

  • Liam Cribbin,
  • Brendan Twamley,
  • Nicolae Buga,
  • John E. O’ Brien,
  • Raphael Bühler,
  • Roland A. Fischer and
  • Mathias O. Senge

Beilstein J. Org. Chem. 2024, 20, 2784–2798, doi:10.3762/bjoc.20.234

Graphical Abstract
  • ][5]. Nonplanar porphyrins offer a marked difference in chemical and physical properties when compared to their planar compatriots [6], with relatively smaller HOMO–LUMO gaps resulting in an observed bathochromic shift in the UV–vis absorption spectrum [7]. The phenomenon of nonplanarity results from
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Published 04 Nov 2024

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

  • Ivana Weisheitelová,
  • Radek Cibulka,
  • Marek Sikorski and
  • Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

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  • potent, biologically active compounds. Interestingly, the introduction of a strong methoxy group at position 7 of the 5-aryldeazaalloxazine core led to a bathochromic shift in the absorption spectra of the synthesised molecules, making them more suitable for visible light photocatalysis. Experimental
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Published 31 Jul 2024

Synthesis and optical properties of bis- and tris-alkynyl-2-trifluoromethylquinolines

  • Stefan Jopp,
  • Franziska Spruner von Mertz,
  • Peter Ehlers,
  • Alexander Villinger and
  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 1246–1255, doi:10.3762/bjoc.20.107

Graphical Abstract
  • , respectively. A bathochromic shift is observed from 9a over 6a to 12a in the first absorption maximum with a total of 0.29 eV. This trend can be observed in the emission spectrum as well. All three emission spectra are characterized by a single broad emission peak which is almost identical for 6a and 12a and
  • and 12a are almost identical in their emission. The influence of the type of substituent located at the alkyne moieties of 12a, 12c, and 12e was also studied. The intensity increases from 12a to 12e and a bathochromic shift of the absorption maxima can be observed. Interestingly, the emission spectra
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Published 29 May 2024

Novel route to enhance the thermo-optical performance of bicyclic diene photoswitches for solar thermal batteries

  • Akanksha Ashok Sangolkar,
  • Rama Krishna Kadiyam and
  • Ravinder Pawar

Beilstein J. Org. Chem. 2024, 20, 1053–1068, doi:10.3762/bjoc.20.93

Graphical Abstract
  • bathochromic shift in the excitation wavelength is also noticed with increasing polarity of the solvents. The red-shift of 7.56 to 12.30 nm is observed in the presence of highly polar acetonitrile. Noteworthy, the absorption onset of the bicyclic diene of type-Ic and IIc is red-shifted to 305 and 304 nm
  • –18.83 kJ/mol). Surprisingly, the energy storage capacity of the type-IIa (5.20 kJ/mol) and IIc (3.14 kJ/mol) photoswitches appreciably increases with the polarity of the solvent without compromising the TBR barrier. The solvation of studied photoswitching systems displays a bathochromic shift in the
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Published 13 May 2024

Synthesis and properties of 6-alkynyl-5-aryluracils

  • Ruben Manuel Figueira de Abreu,
  • Till Brockmann,
  • Alexander Villinger,
  • Peter Ehlers and
  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

Graphical Abstract
  • spectra were investigated. As explained in the previous section, a similar behavior was observed in the emission spectra with respect to the substitution pattern. In general, a bathochromic shift of the emission was observed in the presence of a dimethylamino group at the 5-position. The bathochromic
  • bathochromic shift of 5m is 57 nm and lies between the two emission peaks of 5d and 5k. Therefore, it can be concluded that combining the two substitution patterns leads to this intermediate behavior. Substitution of the 5-π-donor with a π-acceptor group reduced the bathochromic shift from 57 nm to 18 nm
  • shift of 5d compared to its regioisomer 5k is 68 nm. This underlines the spectral effect of the π-donor on the 5- or 6-position and the dependence of the distance between the functional group and the uracil core system. In the spectra of 5m, a combination of both situations can be observed. The
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Published 22 Apr 2024

Switchable molecular tweezers: design and applications

  • Pablo Msellem,
  • Maksym Dekthiarenko,
  • Nihal Hadj Seyd and
  • Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

Graphical Abstract
  • chiroptical properties with a large change in the absorption spectra and a bathochromic shift in the emission maximum. This system represents a rare example of a multi-output readout system, showing responses in ECD, fluorescence, and CPL activity. The authors later reported a similar system with a bipyridine
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Published 01 Mar 2024

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

Graphical Abstract
  • color of these dyes, as shown by the absorption maxima positions of the substituted indigo derivatives (Table 1) [23][24]. The introduction of the ED (electron-donating) substituents into the para (5,5')- or ortho (7,7')-positions to the electron-donating NH group results in a bathochromic shift of the
  • causes a hypsochromic shift of the absorption band, while the presence of the EA substituents at these positions leads to a bathochromic shift (Figure 5). In addition, electron-donating substituents on the nitrogen atom produce bathochromic shifts, while electron-withdrawing groups at this position give
  • the electron density on the N atom in the ground state due to the electronic effects of substituents facilitates charge transfer during excitation, which leads to a decrease in the energy of the transition and a bathochromic shift of the absorption band, and vice versa. Photochemistry of indigo
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Published 07 Feb 2024

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

Graphical Abstract
  • derivatives 2b–g showed a slight bathochromic shift mostly in the range of λmax = 333–360 nm, whereas for the nitro-substituted compound 2a a stronger red shift of the absorption maximum was observed, presumably caused by the strong electron-withdrawing property of the nitro group resulting in a more
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Published 18 Jan 2024

Biphenylene-containing polycyclic conjugated compounds

  • Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

Graphical Abstract
  • clear evidence of a bathochromic shift and a reduction in the optical band gap. These results support the idea that the introduction of biphenylene linkages may decrease delocalization in the structure. However, despite this reduction, there is still communication between the acene units evident from
  • the failure in the formation of the desired target products. Upon comparing the UV–vis absorbance graphs of compounds 28 and 29, POA 29 (λmax = 500 nm), which was obtained through the aromatization of compound 28, exhibited a significant bathochromic shift. These observations further support the
  • nearly identical absorption profiles with a maximum absorption at λmax = 515 nm, the incorporation of donor groups in compound 34c led to a noteworthy bathochromic shift with a maximum absorption at λmax = 534 nm. Additionally, it was reported that all three compounds, 34a–c, demonstrated remarkable
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Published 13 Dec 2023

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

  • Kathryn M. Wolfe,
  • Shahidul Alam,
  • Eva German,
  • Fahad N. Alduayji,
  • Maryam Alqurashi,
  • Frédéric Laquai and
  • Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

Graphical Abstract
  • position (PDIN-B, CN-PDIN-B) with those with a pentafluorobenzyl group (PDIN-FB, CN-PDIN-FB), a bathochromic shift of 0.02 eV is observed when going from the pentafluorobenzyl to the benzyl derivatives. When comparing the derivatives with (CN-PDIN-FB, CN-PDIN-B) and without (PDIN-FB, PDIN-B) a nitrile
  • group, a bathochromic shift of 13 nm is observed for PDIN-FB → CN-PDIN-FB, and a bathochromic shift of 13 nm is observed for PDIN-B → CN-PDIN-B. The presence of the nitrile functional group results in a lowering of the energy of the optical band gap, which can be attributed to a higher degree of
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Published 26 Oct 2023

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

  • Chandra Sekhar Tekuri,
  • Pargat Singh and
  • Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

Graphical Abstract
  • spectroscopy. The preliminary photophysical results revealed a significant red-shift in their absorption and emission spectra as compared to the meso-tetrakis(4-methylphenyl)porphyrins due to the extended π-conjugation. Keywords: bathochromic shift; benzo[f]chromeno[2,3-h]quinoxalinoporphyrins; catalysis
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Published 11 Aug 2023

Direct C2–H alkylation of indoles driven by the photochemical activity of halogen-bonded complexes

  • Martina Mamone,
  • Giuseppe Gentile,
  • Jacopo Dosso,
  • Maurizio Prato and
  • Giacomo Filippini

Beilstein J. Org. Chem. 2023, 19, 575–581, doi:10.3762/bjoc.19.42

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  • charge transfer state which results in a bathochromic shift of the absorption towards the visible range [19][20]. Upon light irradiation, the EDA complex may undergo an intramolecular single-electron-transfer (SET) process to produce a radical ion pair (D•+, A•−). To avoid the occurrence of a back
  • observed that the addition of DABCO to the solution of 2a induced a bathochromic shift of the absorption spectrum towards the visible region, thus indicating the formation of an EDA complex between these chemical species. Importantly, we also confirmed that indole 1a and 2a do not form a photoactive EDA
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Published 27 Apr 2023

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

  • Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

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  • -base porphyrins 23b–29b in good yields. In addition, their zinc analogues 23c–25c were also obtained in excellent yields by the reaction of free-base porphyrins with zinc acetate. The preliminary photophysical studies of the porphyrin-xanthone dyads show a bathochromic shift in the absorption and
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Published 22 Mar 2023

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

  • Sasha Hayes,
  • Aya C. Taki,
  • Kah Yean Lum,
  • Joseph J. Byrne,
  • Merrick G. Ekins,
  • Robin B. Gasser and
  • Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

Graphical Abstract
  • data with related previously reported purealidins [19]. While no HMBC correlations were identified for these exchangeable proton signals, the presence of a phenol was further supported by a bathochromic shift that was seen in the UV spectrum of 1 upon addition of base [20]. The bromine atom and phenol
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Published 15 Nov 2022

Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

  • Oleg A. Levitskiy,
  • Olga I. Aglamazova,
  • Yuri K. Grishin and
  • Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2022, 18, 1166–1176, doi:10.3762/bjoc.18.121

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  • significant bathochromic shift as compared to the deprotonated glycine complex (λmax = 458 nm [9]) indicates an elongation of the conjugation chain and formation of the anionic complex which can be considered as a vinylog of the parent glycine derivative (Scheme 2) The anionic species formed in the
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Published 08 Sep 2022

Synthesis, optical and electrochemical properties of (D–π)2-type and (D–π)2Ph-type fluorescent dyes

  • Kosuke Takemura,
  • Kazuki Ohira,
  • Taiki Higashino,
  • Keiichi Imato and
  • Yousuke Ooyama

Beilstein J. Org. Chem. 2022, 18, 1047–1054, doi:10.3762/bjoc.18.106

Graphical Abstract
  • level of OTT-2 is lower than that of OTK-2, but OTT-2 and OTK-2 have comparable highest occupied molecular orbital (HOMO) energy levels. Consequently, this work reveals that compared to the (D–π)2Ph-type structure, the (D–π)2-type structure exhibits not only a bathochromic shift of the photoabsorption
  • . However, the knr-solid/kr-solid value (3.2) of OTT-2 is smaller than that (5.7) of OTK-2, suggesting that the higher Φfl-solid value of OTT-2 is due to the larger kr value compared with that of OTK-2. Therefore, it was found that the (D–π)2-type structure exhibits not only the bathochromic shift of
  • -2 than OTK-2, that is, the bathochromic shift of the photoabsorption band from OTT-2 to OTK-2. Conclusion We have developed the (D–π)2-type fluorescent dye OTT-2 and the (D–π)2Ph-type fluorescent dye OTK-2 and evaluated their optical and electrochemical properties. Both in solution and the solid
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Published 18 Aug 2022

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

  • Hengjia Liu and
  • Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

Graphical Abstract
  • colors of green (524 nm), yellow (576 nm), red (640 nm), and NIR (739 nm) (Figure 3b) [27]. The stronger Lewis acidity resulted in a stronger emission and bathochromic shift when comparing the effects of BCF and B(C6H5)3 on the optoelectronic properties of the organic UV fluorescent material 35DCzPPy (14
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Published 12 Jul 2022

Towards new NIR dyes for free radical photopolymerization processes

  • Haifaa Mokbel,
  • Guillaume Noirbent,
  • Didier Gigmes,
  • Frédéric Dumur and
  • Jacques Lalevée

Beilstein J. Org. Chem. 2021, 17, 2067–2076, doi:10.3762/bjoc.17.133

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  • [cd]indol-1-ium unit: a bathochromic shift of ≈100 nm was found for these two dyes, as compared to the other dyes investigated in this work, absorbing up to 850 nm. The latter, CBPh3, CI3, and CI10, exhibit a strong absorption above 850 nm (900–1000 nm) and a relatively low absorption at 785 nm
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Published 16 Aug 2021

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

  • Najeh Tka,
  • Mohamed Adnene Hadj Ayed,
  • Mourad Ben Braiek,
  • Mahjoub Jabli,
  • Noureddine Chaaben,
  • Kamel Alimi,
  • Stefan Jopp and
  • Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

Graphical Abstract
  • , derivatives 4e and 4f bearing an electron-deficient fluoro or trifluoromethyl group show a hyperchromic shift of their bands located between 340 and 380 nm. In case of the electron-donating methoxy substituent (4g), a bathochromic shift was observed. Besides, a new band appeared at 321 nm which may be
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Published 16 Jul 2021

Naphthalonitriles featuring efficient emission in solution and in the solid state

  • Sidharth Thulaseedharan Nair Sailaja,
  • Iván Maisuls,
  • Jutta Kösters,
  • Alexander Hepp,
  • Andreas Faust,
  • Jens Voskuhl and
  • Cristian A. Strassert

Beilstein J. Org. Chem. 2020, 16, 2960–2970, doi:10.3762/bjoc.16.246

Graphical Abstract
  • in the cases of Me and t-Bu compounds, where a gradual bathochromic shift in emission is observed with growing water fraction (Figures S35 and S36, Supporting Information File 1), pointing to a slight charge-transfer character of the emissive state. These compounds show a prominent AIEE upon
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Published 02 Dec 2020
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