{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T10:36:59Z","timestamp":1760524619404,"version":"build-2065373602"},"reference-count":78,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2024,5,19]],"date-time":"2024-05-19T00:00:00Z","timestamp":1716076800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Materials"],"abstract":"<jats:p>Advances in electronics and medical diagnostics have made organic dyes extremely popular as key functional materials. From a practical viewpoint, it is necessary to assess the spectroscopic and physicochemical properties of newly designed dyes. In this context, the condensation of 1,3-dimethylbarbituric acid with electron-rich alkylaminobenzaldehyde derivatives has been described, resulting in a series of merocyanine-type dyes. These dyes exhibit intense blue-light absorption but weak fluorescence. An electron-donating alkylamino group at position C4 is responsible for the solvatochromic behavior of the dyes since the lone electron pair of the nitrogen atom is variably delocalized toward the barbituric ring, which exhibits electron-withdrawing properties. This was elucidated, taking into account the different geometry of the amino group. The intramolecular charge transfer in the molecules is responsible for the relatively high redshift in absorption and fluorescence spectra. Additionally, an increase in solvent polarity moves the absorption and fluorescence to lower energy regions. The observed solvatochromism is discussed in terms of the four-parameter Catal\u00e1n solvent polarity scale. The differences in the behavior of the dyes were quantified with the aid of time-dependent density functional theory calculations. The obtained results made it possible to find regularities linking the basic spectroscopic properties of the compounds with their chemical structure. This is important in the targeted search for new, practically important dyes.<\/jats:p>","DOI":"10.3390\/ma17102447","type":"journal-article","created":{"date-parts":[[2024,5,20]],"date-time":"2024-05-20T06:31:58Z","timestamp":1716186718000},"page":"2447","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["The Influence of the Alkylamino Group on the Solvatochromic Behavior of 5-(4-substituted-arylidene)-1,3-dimethylpyrimidine-2,4,6-triones: Synthesis, Spectroscopic and Computational Studies"],"prefix":"10.3390","volume":"17","author":[{"given":"Ilona","family":"Pyszka","sequence":"first","affiliation":[{"name":"Faculty of Chemical Technology and Engineering, Bydgoszcz University of Science and Technology, Seminaryjna 3, 85-326 Bydgoszcz, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3387-2820","authenticated-orcid":false,"given":"Przemys\u0142aw","family":"Krawczyk","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, Collegium Medicum, Nicolaus Copernicus University, Kurpi\u0144skiego 5, 85-950 Bydgoszcz, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3406-5828","authenticated-orcid":false,"given":"Beata","family":"J\u0119drzejewska","sequence":"additional","affiliation":[{"name":"Faculty of Chemical Technology and Engineering, Bydgoszcz University of Science and Technology, Seminaryjna 3, 85-326 Bydgoszcz, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,5,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1134\/S0030400X08010086","article-title":"Electronic structure and fluorescent properties of malononitrile-based merocyanines with positive and negative solvatochromism","volume":"104","author":"Ishchenko","year":"2008","journal-title":"Opt. Spectrosc."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"276413","DOI":"10.1155\/2013\/276413","article-title":"Synthesis and Evaluation of Changes Induced by Solvent and Substituent in Electronic Absorption Spectra of New Azo Disperse Dyes Containig Barbiturate Ring","volume":"2013","author":"Hamidian","year":"2013","journal-title":"J. Spectrosc."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1973","DOI":"10.1021\/cr990402t","article-title":"Cyanines during the 1990s:\u2009 A Review","volume":"100","author":"Mishra","year":"2000","journal-title":"Chem. Rev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"7768","DOI":"10.1021\/acs.chemrev.6b00001","article-title":"Recent Development of Chemosensors Based on Cyanine Platforms","volume":"116","author":"Sun","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1070\/RC2009v078n02ABEH003900","article-title":"Merocyanine dyes: Synthesis, structure, properties and applications","volume":"78","author":"Kulinich","year":"2009","journal-title":"Russ. Chem. Rev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"929","DOI":"10.1016\/j.dyepig.2011.03.019","article-title":"Synthesis and colour spectrophotometric measurements of some novel merocyanine dyes","volume":"92","author":"Shindy","year":"2012","journal-title":"Dyes Pigm."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1016\/j.jphotochem.2007.12.003","article-title":"Structure and fluorescent properties of merocyanines based on N,N-diethylthiobarbituric acid","volume":"197","author":"Kulinich","year":"2008","journal-title":"J. Photochem. Photobiol. A Chem."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"J\u0119drzejewska, B., and Wejnerowska, G. (2020). Highly Effective Sensitizers Based on Merocyanine Dyes for Visible Light Initiated Radical Polymerization. Polymers, 12.","DOI":"10.3390\/polym12061242"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"601","DOI":"10.1016\/j.bmcl.2013.12.013","article-title":"Synthesis and anti-proliferative activity of aromatic substituted 5-((1-benzyl-1H-indol-3-yl)methylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione analogs against human tumor cell lines","volume":"24","author":"Madadi","year":"2014","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1007\/s12039-021-02007-z","article-title":"Effect of substitution on the binding affinity of 5-bezylidenebarbituric acid derivatives to ctDNA: In silico and in vitro studies","volume":"134","author":"Dastan","year":"2022","journal-title":"J. Chem. Sci."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"506","DOI":"10.1007\/s11094-018-1849-7","article-title":"Synthesis and Antimicrobial Activity of 5-(Arylmethylidene)-2,4,6-Pyrimidine-2,4,6(1H,3H,5H)-Triones","volume":"52","author":"Luzhnova","year":"2018","journal-title":"Pharm. Chem. J."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3939","DOI":"10.1016\/j.tet.2017.05.070","article-title":"Br\u00f8nsted acid mediated cyclizations of ortho-aryl(ethynyl)pyrimidines","volume":"73","author":"Shestakov","year":"2017","journal-title":"Tetrahedron"},{"key":"ref_13","unstructured":"Lindon, J.C., Tranter, G.E., and Koppenaal, D.W. (2017). Encyclopedia of Spectroscopy and Spectrometry, Academic Press. [3rd ed.]."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"541","DOI":"10.1515\/zna-1955-0707","article-title":"Dipolmoment und elektronenstruktur von angeregten molek\u00fclen","volume":"10a","author":"Lippert","year":"1955","journal-title":"Z. Naturforsch."},{"key":"ref_15","first-page":"962","article-title":"Spektroskopische bestimmung des dipolmomentes aromatischer verbindungen im ersten angeregten singulettzustand","volume":"61","author":"Lippert","year":"1957","journal-title":"Ber. Bunsenges. Phys. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"465","DOI":"10.1246\/bcsj.29.465","article-title":"Solvent Effects upon Fluorescence Spectra and the Dipolemoments of Excited Molecules","volume":"29","author":"Mataga","year":"1956","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"562","DOI":"10.1021\/j150551a012","article-title":"Theory of Solvent Effects on Molecular Electronic Spectra. Frequency Shifts","volume":"61","author":"McRae","year":"1957","journal-title":"J. Phys. Chem."},{"key":"ref_18","first-page":"379","article-title":"Universal molecular interactions and their effect on the position of the electronic spectra of molecules in two-component solutions","volume":"10","author":"Bakhshiev","year":"1961","journal-title":"Opt. Spectrosc. (USSR)"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"621","DOI":"10.1515\/zna-1962-0713","article-title":"Zur Theorie des Einflusses von L\u00f6sungsmitteln auf die Elektronenspektren der Molek\u00fcle","volume":"17A","author":"Bilot","year":"1962","journal-title":"Z. Naturforsch."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"256","DOI":"10.1515\/zna-1963-0228","article-title":"Dipolmomente einiger Phthalimid-Derivate im ersten angeregten Singulettzustand","volume":"18A","author":"Bilot","year":"1963","journal-title":"Z. Naturforsch."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"985","DOI":"10.1016\/j.saa.2011.04.010","article-title":"Dipole moment determination of 4-[N-(5,6,7,8-tetrahydroisoquinolinium-5-ylidene)methyl]-N,N-dialkylaniline iodides in solution","volume":"79","author":"Pietrzak","year":"2011","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2319","DOI":"10.1021\/cr00032a005","article-title":"Solvatochromic Dyes as Solvent Polarity Indicators","volume":"94","author":"Reichardt","year":"1994","journal-title":"Chem. Rev."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Reichardt, C. (2003). Solvents and Solvent Effects in Organic Chemistry, WILEY-VCH Verlag GmbH & Co. KGaA. [3rd ed.].","DOI":"10.1002\/3527601791"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1610","DOI":"10.1039\/c1pp05123g","article-title":"Influence of substituents on the nitrogen atom of 3-[2-(4-aminophenyl)benzoxazol-5-yl]alanine derivatives on their photophysical properties-solvatochromic studies","volume":"10","author":"Guzow","year":"2011","journal-title":"Photochem. Photobiol. Sci."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"9133","DOI":"10.1021\/j100088a007","article-title":"Excited State Dipole Moments from an Efficient Analysis of Solvatochromic Stokes Shift Data","volume":"98","author":"Ravi","year":"1994","journal-title":"J. Phys. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/S1386-1425(00)00330-9","article-title":"Excited-state dipole moments of some hydroxycoumarin dyes using an efficient solvatochromic method based on the solvent polarity parameter, ETN","volume":"57","author":"Kumar","year":"2001","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_27","unstructured":"Suppan, P., and Ghoneim, N. (1997). Solvatochromism, Royal Society of Chemistry."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1021\/cr020750m","article-title":"Quantitative measures of solvent polarity","volume":"104","author":"Katritzky","year":"2004","journal-title":"Chem. Rev."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"4694","DOI":"10.1002\/ejoc.200400311","article-title":"Empirical treatment of the inductive and dispersive components of solute\u2212solvent interactions: The solvent polarizability (SP) scale","volume":"2004","author":"Hopf","year":"2004","journal-title":"Eur. J. Org. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1785","DOI":"10.1002\/jlac.199619961112","article-title":"A Generalized Solvent Basicity Scale: The Solvatochromism of 5-Nitroindoline and Its Homomorph 1-Methyl-5-nitroindoline","volume":"1996","year":"1996","journal-title":"Liebigs Ann."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"5951","DOI":"10.1021\/jp8095727","article-title":"Toward a Generalized Treatment of the Solvent Effect Based on Four Empirical Scales: Dipolarity (SdP, a New Scale), Polarizability (SP), Acidity (SA), and Basicity (SB) of the Medium","volume":"113","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"377","DOI":"10.1021\/ja00418a009","article-title":"The solvatochromic comparison method. I. The.beta.-scale of solvent hydrogen-bond acceptor (HBA) basicities","volume":"98","author":"Kamlet","year":"1976","journal-title":"J. Am. Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"485","DOI":"10.1002\/9780470171929.ch6","article-title":"An examination of linear solvation energy relationships","volume":"13","author":"Kamlet","year":"1981","journal-title":"Prog. Phys. Org. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2886","DOI":"10.1021\/ja00426a036","article-title":"The solvatochromic comparison method. 2. The. alpha.-scale of solvent hydrogen-bond donor (HBD) acidities","volume":"98","author":"Taft","year":"1976","journal-title":"J. Am. Chem. Soc."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1080\/00304949809355310","article-title":"Efficiency of the Vilsmeier-Haack method in the synthesis of p-aminobenzaldehydes","volume":"30","author":"Gawinecki","year":"1998","journal-title":"Org. Prep. Proced. Int."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"150","DOI":"10.1016\/j.dyepig.2016.08.046","article-title":"Photostability of push-pull phenanthroimidazole derivative upon one- and two-photon excitation","volume":"136","author":"Gordel","year":"2017","journal-title":"Dyes Pigm."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2213","DOI":"10.1351\/PAC-REP-10-09-31","article-title":"Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report)","volume":"83","author":"Brouwer","year":"2011","journal-title":"Pure Appl. Chem."},{"key":"ref_38","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). Gaussian 16, Revision C.01, Gaussian, Inc."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2889","DOI":"10.1063\/1.479571","article-title":"Accurate excitation energies from time-dependent density functional theory: Assessing the PBE0 model","volume":"111","author":"Adamo","year":"1999","journal-title":"J. Chem. Phys."},{"key":"ref_40","unstructured":"Guido, C., and Caprasecca, S. (2016). Corrected Linear Response. State-Specific Correction to Solvent Polarization Response, Molecolab."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"117757","DOI":"10.1016\/j.saa.2019.117757","article-title":"2\u2032-(1H-phenanthro [9,10-d]imidazol-2-yl)-phenyl-4-carboxylic acid N-hydroxysuccinimide ester: A new phenanthroimidazole derivative as a fluorescent probe for medical imaging applications","volume":"228","author":"Krawczyk","year":"2020","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"473","DOI":"10.1039\/c9pp00478e","article-title":"4-(4-Chloro-2-oxo-3(1H-phenanthro[9,10-d] imidazol-2-yl)-2H-chromen-6-yl)benzaldehyde as a fluorescent probe for medical imaging: Linear and nonlinear optical properties","volume":"19","author":"Krawczyk","year":"2020","journal-title":"Photochem. Photobiol. Sci."},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Krawczyk, P., J\u0119drzejewska, B., Seklecka, K., Cytarska, J., and \u0141\u0105czkowski, K.Z. (2021). Effect of the Chloro-Substitution on Electrochemical and Optical Properties of New Carbazole Dyes. Materials, 14.","DOI":"10.3390\/ma14113091"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"117910","DOI":"10.1016\/j.jlumin.2021.117910","article-title":"Influence of N-donor substituents on physicochemical properties of phenanthro[9,10-d]imidazole derivatives","volume":"233","author":"Kula","year":"2021","journal-title":"J. Lumin."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1742","DOI":"10.1021\/acs.jpcb.1c08056","article-title":"Multifunctional Oxazolone Derivative as an Optical Amplifier, Generator, and Modulator","volume":"126","author":"Szukalski","year":"2022","journal-title":"J. Phys. Chem. B"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"7319","DOI":"10.1021\/acs.joc.2c00500","article-title":"A Modified Oxazolone Dye Dedicated to Spectroscopy and Optoelectronics","volume":"87","author":"Szukalski","year":"2022","journal-title":"J. Org. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"2498","DOI":"10.1021\/ct200308m","article-title":"A Qualitative Index of Spatial Extent in Charge-Transfer Excitations","volume":"7","author":"Adamo","year":"2011","journal-title":"J. Chem. Theory Comput."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3032","DOI":"10.1063\/1.474659","article-title":"A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics","volume":"107","author":"Mennucci","year":"1997","journal-title":"J. Chem. Phys."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1016\/j.saa.2012.11.033","article-title":"PCM\/TD-DFT analysis of 1-bromo-2,3-dichlorobenzene-A combined study of experimental (FT-IR and FT-Raman) and theoretical calculations","volume":"105","author":"Arivazhagan","year":"2013","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"8943","DOI":"10.1021\/jo0351670","article-title":"Merocyanine Dyes Containing Imide Functional Groups:\u2009 Synthesis and Studies on Hydrogen Bonding to Melamine Receptors","volume":"68","author":"Yao","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Ding, S., Yao, B., Schobben, L., and Hong, Y. (2020). Barbituric Acid Based Fluorogens: Synthesis, Aggregation-Induced Emission, and Protein Fibril Detection. Molecules, 25.","DOI":"10.3390\/molecules25010032"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1183","DOI":"10.1016\/S1386-1425(00)00461-3","article-title":"Merocyanine-type dyes from barbituric acid derivatives","volume":"57","author":"Rezende","year":"2001","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"2373","DOI":"10.1016\/j.bmcl.2008.02.066","article-title":"Synthesis of barbiturate-based methionine aminopeptidase-1 inhibitors","volume":"18","author":"Haldar","year":"2008","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"9170","DOI":"10.1021\/jo071273g","article-title":"Electrophilicity of 5-Benzylidene-1,3-dimethylbarbituric and -thiobarbituric Acids","volume":"72","author":"Seeliger","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"117168","DOI":"10.1016\/j.saa.2019.117168","article-title":"Detection of nitroaromatics based on aggregation induced emission of barbituric acid derivatives","volume":"222","author":"Zhang","year":"2019","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Wr\u00f3blewski, S., Trzebiatowska, K., J\u0119drzejewska, B., Pietrzak, M., Gawinecki, R., and P\u0105czkowski, J. (1999). Development of fluorescence probes based on stilbazolium salts for monitoring free radical polymerization processes. J. Chem. Soc. Perkin Trans. 2, 1909\u20131917.","DOI":"10.1039\/a902904d"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/S0143-7208(00)00012-7","article-title":"The effect of the amino group on the spectral properties of substituted styrylpyridinium salts","volume":"45","author":"Gawinecki","year":"2000","journal-title":"Dyes Pigm."},{"key":"ref_58","doi-asserted-by":"crossref","unstructured":"Gawinecki, R., Kolehmainen, E., and Kauppinen, R. (1998). 1H and 13C NMR studies of para-substituted benzaldoximes for evaluation of the electron donor properties of substituted amino groups\u2020. J. Chem. Soc. Perkin Trans. 2, 25\u201330.","DOI":"10.1039\/a705668k"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"7779","DOI":"10.1021\/acs.joc.8b00664","article-title":"Influence of the Nature of the Amino Group in Highly Fluorescent Difluoroborates Exhibiting Intramolecular Charge Transfer","volume":"83","author":"Skotnicka","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"1173","DOI":"10.1002\/poc.1689","article-title":"Conformational pathways of simple six-membered rings","volume":"23","author":"Stortz","year":"2010","journal-title":"J. Phys. Org. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"26403","DOI":"10.1039\/C7CP05244H","article-title":"Coherence in nonradiative transitions: Internal conversion in Rydberg-excited N-methyl and N-ethyl morpholine","volume":"19","author":"Zhang","year":"2017","journal-title":"PCCP"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"27417","DOI":"10.1039\/D1CP04236J","article-title":"Ultrafast conformational dynamics of Rydberg-excited N-methyl piperidine","volume":"23","author":"Du","year":"2021","journal-title":"PCCP"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1007\/s10895-009-0524-5","article-title":"Solvent Effects on the Spectroscopic Properties of Styrylquinolinium Dyes Series","volume":"20","author":"Pietrzak","year":"2010","journal-title":"J. Fluoresc."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"315","DOI":"10.1016\/0009-2614(73)80367-7","article-title":"Reinterpretation of the anomalous fluorescense of p-n,n-dimethylamino-benzonitrile","volume":"19","author":"Rotkiewicz","year":"1973","journal-title":"Chem. Phys. Lett."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"3899","DOI":"10.1021\/cr940745l","article-title":"Structural Changes Accompanying Intramolecular Electron Transfer:\u2009 Focus on Twisted Intramolecular Charge-Transfer States and Structures","volume":"103","author":"Grabowski","year":"2003","journal-title":"Chem. Rev."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"9248","DOI":"10.1039\/C4CP02381A","article-title":"The driving forces for twisted or planar intramolecular charge transfer","volume":"17","author":"Zhong","year":"2015","journal-title":"PCCP"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"366","DOI":"10.1021\/acs.accounts.6b00517","article-title":"Solvatochromic and Fluorogenic Dyes as Environment-Sensitive Probes: Design and Biological Applications","volume":"50","author":"Klymchenko","year":"2017","journal-title":"Acc. Chem. Res."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"86","DOI":"10.1016\/j.saa.2018.03.048","article-title":"Spectral and physicochemical properties of difluoroboranyls containing N,N-dimethylamino group studied by solvatochromic methods","volume":"199","author":"Grabarz","year":"2018","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"258","DOI":"10.1016\/j.saa.2016.08.006","article-title":"Experimental and theoretical studies of the influence of solvent polarity on the spectral properties of two push-pull oxazol-5-(4H)-one compounds","volume":"171","author":"Krawczyk","year":"2017","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"527","DOI":"10.1016\/j.saa.2011.05.102","article-title":"Comments on the determination of excited state dipole moment of molecules using the method of solvatochromism","volume":"82","author":"Kawski","year":"2011","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"1396","DOI":"10.1021\/ar100043u","article-title":"Spectral Engineering in \u03c0-Conjugated Polymers with Intramolecular Donor\u2212Acceptor Interactions","volume":"43","author":"Beaujuge","year":"2010","journal-title":"Acc. Chem. Res."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"3805","DOI":"10.1021\/cm201424a","article-title":"Donor\u2013Acceptor\u2013Donor-based \u03c0-Conjugated Oligomers for Nonlinear Optics and Near-IR Emission","volume":"23","author":"Ellinger","year":"2011","journal-title":"Chem. Mater."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"6864","DOI":"10.1021\/j100196a004","article-title":"Twisted internal charge transfer in (aminophenyl)pyridinium","volume":"96","author":"Fromherz","year":"1992","journal-title":"J. Phys. Chem."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"e3909","DOI":"10.1002\/poc.3909","article-title":"Impact of electron-withdrawing and electron-donating substituents on the electrochemical and charge transport properties of indacenodithiophene-based small molecule acceptors for organic solar cells","volume":"32","author":"Tahir","year":"2019","journal-title":"J. Phys. Org. Chem."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1021\/jp104596v","article-title":"Photophysical Properties of a Series of Electron-Donating and -Withdrawing Platinum Acetylide Two-Photon Chromophores","volume":"115","author":"Haley","year":"2011","journal-title":"J. Phys. Chem. A"},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1016\/j.jphotochem.2006.12.014","article-title":"Electronic structure and solvatochromism of merocyanines based on N,N-diethylthiobarbituric acid","volume":"188","author":"Kulinich","year":"2007","journal-title":"J. Photochem. Photobiol. A Chem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"264","DOI":"10.1002\/poc.1163","article-title":"Synthesis, properties, and solvatochromism of 1,3-dimethyl-5-{(thien-2-yl)-[4-(1-piperidyl) phenyl]methylidene}-(1H,3H)-pyrimidine-2,4,6-trione","volume":"20","author":"Spange","year":"2007","journal-title":"J. Phys. Org. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1016\/j.saa.2006.10.043","article-title":"Electronic structure and solvatochromism of merocyanines: NMR spectroscopic point of view","volume":"68","author":"Kulinich","year":"2007","journal-title":"Spectrochim. 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