Tuning the Solid Phase Fluorescence Emission from Long Wavelength Visible to Near-Infrared in Oxazol-5-One Derivatives: Structure-Property Relationship, Theoretical and Experimental Studies.

Aggregation induced enhanced emission (AIEE) Noncovalent interactions Solid state long wavelength visible and near infrared fluorescence Stacking interactions

Journal

Journal of fluorescence
ISSN: 1573-4994
Titre abrégé: J Fluoresc
Pays: Netherlands
ID NLM: 9201341

Informations de publication

Date de publication:
Jul 2023
Historique:
received: 21 12 2022
accepted: 25 01 2023
medline: 11 2 2023
pubmed: 11 2 2023
entrez: 10 2 2023
Statut: ppublish

Résumé

Most of the fluorescent molecules among organic [Formula: see text]-conjugated materials show blue or green emission in the solid phase but few of them emit red-shifted visible and near-infrared light in the material science. To create molecules emitting for this feature, two π-conjugated oxazol-5-one derivatives containing donor (OCH

Identifiants

pubmed: 36763296
doi: 10.1007/s10895-023-03158-7
pii: 10.1007/s10895-023-03158-7
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

1481-1494

Informations de copyright

© 2023. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.

Références

Serhan M, Sprowls M, Jackemeyer D, Long M, Perez ID, Maret W, Tao N, Forzani E (2019) Total iron measurement in human serum with a smartphone. AIChE Annu Meet Conf Proc 8:2800309. https://doi.org/10.1039/x0xx00000x
doi: 10.1039/x0xx00000x
Kim HU, Sohn S, Choi W, Kim M, Ryu SU, Park T, Jung S, Bejoymohandas KS (2018) Substituents engineered deep-red to near-infrared phosphorescence from Tris-Heteroleptic Iridium(Iii) complexes for solution processable Red-NIR organic light-emitting diodes. Jo Mater Chem C 6(39):10640–10658. https://doi.org/10.1039/c8tc04321c
doi: 10.1039/c8tc04321c
Kim DY, Song DW, Chopra N, De Somer P, So F (2010) Organic infrared upconversion device. Adv Mater 22(20):2260–2263. https://doi.org/10.1002/adma.200903312
doi: 10.1002/adma.200903312 pubmed: 20352630
Cheng X, Wang K, Huang S, Zhang H, Zhang H, Wang Y (2015) Organic crystals with near-infrared amplified spontaneous emissions based on 2′-hydroxychalcone derivatives: subtle structure modification but great property change. Angew Chem 127(29):8489–8493. https://doi.org/10.1002/ange.201503914
doi: 10.1002/ange.201503914
Qin W, Lam JWY, Yang Z, Chen S, Liang G, Zhao W, Kwok HS, Tang BZ (2015) Red emissive AIE luminogens with high hole-transporting properties for efficient non-doped OLEDs. Chem Commun 51(34):7321–7324. https://doi.org/10.1039/c5cc01690h
doi: 10.1039/c5cc01690h
Zhao Q, Sun JZ (2016) Red and near infrared emission materials with AIE characteristics. J Mater Chem C 4(45):10588–10609. https://doi.org/10.1039/c6tc03359h
doi: 10.1039/c6tc03359h
Jiang J, Li X, Hanif M, Zhou J, Hu D, Su S, Xie Z, Gao Y, Yang B, Ma Y (2017) Pyridal[2,1,3]Thiadiazole as strong electron-withdrawing and less sterically-hindered acceptor for highly efficient donor-acceptor type NIR materials. J Mater Chem C 5(42):11053–11058. https://doi.org/10.1039/c7tc03978f
doi: 10.1039/c7tc03978f
Poddar M, Sivakumar G, Misra R (2019) Donor-acceptor substituted 1,8-naphthalimides: design, synthesis, and structure-property relationship. J Mater Chem C 7(47):14798–14815. https://doi.org/10.1039/c9tc02634g
doi: 10.1039/c9tc02634g
Fenwick O, Fusco S, Baig TN, Di Stasio F, Steckler TT, Henriksson P, Fléchon C, Andersson MR, Cacialli F (2013) Efficient red electroluminescence from diketopyrrolopyrrole copolymerised with a polyfluorene. APL Materials 1(3):032108. https://doi.org/10.1063/1.4820433
doi: 10.1063/1.4820433
Zhao Z, Gao S, Zheng X, Zhang P, Wu W, Kwok RTK, Xiong Y, Leung NLC, Chen Y, Gao X, Lam JWY, Tang BZ (2018) Rational Design of Perylenediimide-Substituted Triphenylethylene to Electron Transporting Aggregation-Induced Emission Luminogens (AIEgens) with High Mobility and Near-Infrared Emission. Adv Func Mater 28(11):1–9. https://doi.org/10.1002/adfm.201705609
doi: 10.1002/adfm.201705609
Massin J, Dayoub W, Mulatier JC, Aronica C, Bretonnière Y, Andraud C (2011) Near-infrared solid-state emitters based on isophorone: synthesis, crystal structure and spectroscopic properties. Chem Mater 23(3):862–873. https://doi.org/10.1021/cm102165r
doi: 10.1021/cm102165r
Lim CK, Kim S, Kwon IC, Ahn CH, Park SY (2009) Dye-condensed biopolymeric hybrids: chromophoric aggregation and self-assembly toward fluorescent bionanoparticles for near infrared bioimaging. Chem Mater 21(24):5819–5825. https://doi.org/10.1021/cm902379x
doi: 10.1021/cm902379x
Baumes JM, Gassensmith JJ, Giblin J, Lee JJ, White AG, Culligan WJ, Leevy WM, Kuno M, Smith BD (2010) Storable, thermally activated, near-infrared chemiluminescent dyes and dye-stained microparticles for optical imaging. Nat Chem 2(12):1025–1030. https://doi.org/10.1038/nchem.871
doi: 10.1038/nchem.871 pubmed: 21107365 pmcid: 3043620
Wu H, Zhao P, Li X, Chen W, Ågren H, Zhang Q, Zhu L (2017) Tuning for visible fluorescence and near-infrared phosphorescence on a unimolecular mechanically sensitive platform via adjustable CH-π interaction. ACS Appl Mater Interfaces 9(4):3865–3872. https://doi.org/10.1021/acsami.6b15939
doi: 10.1021/acsami.6b15939 pubmed: 28073247
Xu S, Duan Y, Liu B (2020) Precise molecular design for high-performance luminogens with aggregation-induced emission. Adv Mater 32(1):1–31. https://doi.org/10.1002/adma.201903530
doi: 10.1002/adma.201903530
Yuan WZ, Lu P, Chen S, Lam JWY, Wang Z, Liu Y, Kwok HS, Yuguang M, Tang BZ (2010) Changing the behavior of chromophores from aggregation-caused quenching to aggregation-induced emission: development of highly efficient light emitters in the solid state. Adv Mater 22(19):2159–2163. https://doi.org/10.1002/adma.200904056
doi: 10.1002/adma.200904056 pubmed: 20564253
Singh A, Lim CK, Lee YD, Maeng JH, Lee S, Koh J, Kim S (2013) Tuning solid-state fluorescence to the near-infrared: a combinatorial approach to discovering molecular nanoprobes for biomedical imaging. ACS Appl Mater Interfaces 5(18):8881–8888. https://doi.org/10.1021/am4012066
doi: 10.1021/am4012066 pubmed: 23731221
Li Q, Li Z (2017) The strong light-emission materials in the aggregated state: what happens from a single molecule to the collective group. Advanced Science 4(7):1–15. https://doi.org/10.1002/advs.201600484
doi: 10.1002/advs.201600484
Zhang H, Zhang Z, Ye K, Zhang J, Wang Y (2006) Organic crystals with tunable emission colors based on a single organic molecule and different molecular packing structures. Adv Mater 18(18):2369–2372. https://doi.org/10.1002/adma.200600704
doi: 10.1002/adma.200600704
Karamertzanis PG, Day GM, Welch GWA, Kendrick J, Leusen FJJ, Neumann MA, Price SL (2008) Modeling the interplay of inter- and intramolecular hydrogen bonding in conformational polymorphs. J Chem Phys 128(24):244708. https://doi.org/10.1063/1.2937446
doi: 10.1063/1.2937446 pubmed: 18601366
Cornil J, Beljonne D, Calbert JP, Brédas JL (2001) Interchain interactions in organic π-Conjugated materials: impact on electronic structure, optical response, and charge transport. Adv Mater 13(14):1053–1067. https://doi.org/10.1002/1521-4095(200107)13:14%3c1053::AID-ADMA1053%3e3.0.CO;2-7
doi: 10.1002/1521-4095(200107)13:14<1053::AID-ADMA1053>3.0.CO;2-7
Peng HQ, Zheng X, Han T, Kwok RTK, Lam JWY, Huang X, Tang BZ (2017) Dramatic differences in aggregation-induced emission and supramolecular polymerizability of tetraphenylethene-based stereoisomers. J Am Chem Soc 139(29):10150–10156. https://doi.org/10.1021/jacs.7b05792
doi: 10.1021/jacs.7b05792 pubmed: 28692263
Mei J, Hong Y, Lam JWY, Qin A, Tang Y, Tang BZ (2014) Aggregation-induced emission: the whole is more brilliant than the parts. Adv Mater 26(31):5429–5479. https://doi.org/10.1002/adma.201401356
doi: 10.1002/adma.201401356 pubmed: 24975272
Li Y, Li F, Zhang H, Xie Z, Xie W, Xu H, Li B, Shen F, Ye L, Hanif M, Ma D, Ma Y (2007) Tight Intermolecular Packing through Supramolecular Interactions in Crystals of Cyano Substituted Oligo(Para-Phenylene Vinylene): a key factor for aggregation-induced emission. Chem Commun 1(3):231–233. https://doi.org/10.1039/b612732k
doi: 10.1039/b612732k
Spano FC (2010) The spectral signatures of frenkel polarons in. Acc Chem Res 43(3):429–439
doi: 10.1021/ar900233v pubmed: 20014774
Xie Z, Yang B, Liu L, Ma Y (2013) J-Type dipole stacking and strong Π-Π interactions in the crystals of distyrylbenzene derivatives: the crystal structures, high luminescence properties and prediction of high mobility. J Mol Eng Mater 01(03):1340002. https://doi.org/10.1142/s2251237313400029
doi: 10.1142/s2251237313400029
Banerjee A, Saha A, Saha BK (2019) Understanding the behavior of π-π interactions in crystal structures in light of geometry corrected statistical analysis: similarities and differences with the theoretical models. Cryst Growth Des 19(4):2245–2252. https://doi.org/10.1021/acs.cgd.8b01857
doi: 10.1021/acs.cgd.8b01857
Dou JH, Zheng YQ, Yao ZF, Yu ZA, Lei T, Shen X, Luo XY, Sun J, Zhang SD, Ding YF, Han G, Yi Y, Wang JY, Pei J (2015) Fine-tuning of crystal packing and charge transport properties of BDOPV derivatives through fluorine substitution. J Am Chem Soc 137(50):15947–15956. https://doi.org/10.1021/jacs.5b11114
doi: 10.1021/jacs.5b11114 pubmed: 26619351
Dong H, Luo M, Wang S, Ma X (2017) Synthesis and properties of tetraphenylethylene derivatived diarylethene with photochromism and aggregation-induced emission. Dyes Pigm 139:118–128
doi: 10.1016/j.dyepig.2016.11.054
Zhao F, Chen Z, Fan C, Liu G, Pu S (2019) Aggregation-induced emission (AIE)-active highly emissive novel carbazolebased dyes with various solid-state fluorescence and reversible mechanofluorochromism characteristics. Dyes Pigm 164:390–397. https://doi.org/10.1002/adma.200700550
doi: 10.1002/adma.200700550
Sevinçek R, Öztürk G, Aygün M, Alp S, Büyükgüngör O (2011) Structural and photophysical characterization, topological and conformational analysis of 2-o-Tolyl-4-(3-N, N-Dimethylaminophenylmethylene)- Oxazol-5-One. J Struct Chem 52(2):405–411. https://doi.org/10.1134/S0022476611020247
doi: 10.1134/S0022476611020247
Saxena G, Chaudhary A, Naqvi A, Khan S, Seth DS (2008) Synthesis, characterization and study of potential reactions of tertiary amino aldehydes. Orient J Chem 24(1):347–351
Icli S, Icil H, Alp S, Koc H, McKillop A, Icli S, Icil H (1994) Nmr, absorption and fluorescence parameters of azlactones. Spectrosc Lett 27(9):1115–1128. https://doi.org/10.1080/00387019408006969
doi: 10.1080/00387019408006969
Nazlı İH, Alp S, Topkaya D, GüneyAfacan İ, Nalbantsoy A (2020) Synthesis and characterization of two novel Oxazol-5-Ones derivatives and their multifunctional properties; PH sensitivity, electropolymerizability and antiproliferative activity. J Fluoresc 30(5):1063–1073. https://doi.org/10.1007/s10895-020-02552-9
doi: 10.1007/s10895-020-02552-9 pubmed: 32617721
S JL, Chemie ADER (1893) Ueber die 1,3-Diketone. Annalen Der Chemie 276:1–8. https://doi.org/10.1002/jlac.18932770104
doi: 10.1002/jlac.18932770104
Li Y, Yang X, Miao J, Sun G (2016) Substitution position and vinylene bond geometry modulating the fluorescence solvatochromism and aggregation-induced emission of ( 9-Anthryl ) Vinyl ( 1-Pyrenyl ) Vinylbenzene Isomers Substitution Position and Vinylene Bond Geometry Modulating the Fluores 120(38):21722–21729. https://doi.org/10.1021/acs.jpcc.6b04392
Yu C, Hsu C, Weng H (2018) RSC advances. RSC Adv 8:12619–12627. https://doi.org/10.1039/C8RA01448E
doi: 10.1039/C8RA01448E pubmed: 35541279 pmcid: 9079628
Ma Y, Sun JZ, Tang BZ (2013) Effects of Substitution with Donor − acceptor groups on the properties of tetraphenylethene trimer: aggregation-induced emission. Solvatochromism Mechanochromism 117(14):7334–7347. https://doi.org/10.1021/jp311360p
doi: 10.1021/jp311360p
Qin A, Sun JZ, Tang BZ (2012) Fumaronitrile-based fluorogen: red to near-infrared fluorescence, aggregation-induced emission, solvatochromism, and twisted intramolecular charge transfer 116(19):10541–10547. https://doi.org/10.1021/jp303100a
Niu C, You Y, Zhao L, He D, Na N, Ouyang J (2015) Solvatochromism, Reversible Chromism and Self-Assembly Effects of Heteroatom-Assisted Aggregation-Induced Enhanced Emission ( AIEE ) Compounds: 13983–13990. https://doi.org/10.1002/chem.201501902
Yuan WZ, Gong Y, Chen S, Shen XY, Lam JWY, Lu P, Lu Y, Wang Z, Hu R, Xie N, Kwok HS, Zhang Y, Sun JZ, Tang BZ (2012) Efficient solid emitters with aggregation-induced emission and intramolecular charge transfer characteristics: molecular design, synthesis, photophysical behaviors, and OLED application. 24(8):1518–1528. https://doi.org/10.1021/cm300416y
Yao Z, Wang J, Pei J (2018) Control of π - π stacking via crystal engineering in organic conjugated small control of π − π stacking via crystal engineering in organic conjugated small molecule crystals published as part of a crystal growth and design virtual special issue on π − π S., No. November 2017. https://doi.org/10.1021/acs.cgd.7b01385
Cheng X, Li F, Han S, Zhang Y, Jiao C, Wei J, Ye K, Wang Y, Zhang H, Cheng X, Li F, Han S, Zhang Y, Jiao C, Wei J, Ye K, Wang Y, Zhang H (2015): 1–8. https://doi.org/10.1038/srep09140
Chen J, Xie Z, Lam JWY, Law CCW, Tang BZ (2003) Silole-containing polyacetylenes. Synthesis, thermal stability, light emission, nanodimensional aggregation, and restricted intramolecular rotation. 36(4):1108–1117. https://doi.org/10.1021/ma0213504
Chen J, Tang BZ (2013) Restricted intramolecular rotations : a mechanism for aggregation-induced emission 20:15349–15353. https://doi.org/10.1002/chem.201403811
Wu H, Zhao P, Li X, Chen W, Ågren H, Zhang Q, Zhu L (2017) Tuning for visible fluorescence and near-infrared phosphorescence on a unimolecular mechanically-sensitive platform via adjustable CH- # interaction tuning for visible fluorescence and near-infrared phosphorescence on a unimolecular mechanically-sensitive 9(4):3865–3872 https://doi.org/10.1021/acsami.6b15939 .
Rountree KJ, Mccarthy BD, Rountree ES, Eisenhart TT, Dempsey JL (2017) A practical beginner’ s guide to cyclic voltammetry, 95(2):197–206. https://doi.org/10.1021/acs.jchemed.7b00361
Soylemez S, Hacioglu SO, Demirci Uzun S, Toppare L (2015) A low band gap benzimidazole derivative and its copolymer with 3 , 4- ethylenedioxythiophene for electrochemical studies a low band gap benzimidazole derivative and its copolymer with 3 , 4-Ethylenedioxythiophene for electrochemical studies 162(1):H6-H14. https://doi.org/10.1149/2.0311501jes
Hacioglu SO (2020) Copolymerization of Azobenzene-Bearing Monomer and 3 , 4- Ethylenedioxythiophene ( EDOT ): improved electrochemical performance for electrochromic device applications 38:109–117. https://doi.org/10.1007/s10118-019-2306-0
Mastragostino M, Arbizzani C, Soavi F (2001) Polymer-based supercapacitors. J Power Sources 98:812–815. https://doi.org/10.1016/S0378-7753(01)00613-9
doi: 10.1016/S0378-7753(01)00613-9
Wang L, Duan G, Ji Y, Zhang H (2012) Electronic and charge transport properties of peri - xanthenoxanthene: The effects of heteroatoms and phenyl substitutions 116(43):22679–22686. https://doi.org/10.1021/jp306326e
Lina H, Jinpeng W, Diandian Z, Peng M, Congming M, Yong P, Juncheng J (2020) Theoretical study on CL-20-based cocrystal energetic compounds in an external electric field. ACS Omega 5(24):14767–14775. https://doi.org/10.1021/acsomega.0c01643
Lee JY, Kim KS, Mhin BJ, Yong J, Kim KS (2001) Intramolecular charge transfer of π-conjugated push – pull systems in terms of polarizability and electronegativity. 115:9484. https://doi.org/10.1063/1.1413986
Ahn M, Kim M, Cho DW, Wee K (2020) Electron push − pull effects on intramolecular charge transfer in perylene-based donor − acceptor compounds 86(1):403–413. https://doi.org/10.1021/acs.joc.0c02149
Szatylowicz H, Stasyuk OA, Krygowski TM (2015) Substituent effects in heterocyclic systems 116:1–56. https://doi.org/10.1016/bs.aihch.2015.05.002
Neetha M, Cherumuttathu HS (2014) A molecular electrostatic potential analysis of hydrogen, halogen, and dihydrogen bonds. J Phys Chem A 118:1697–1705. https://doi.org/10.1021/jp4115699
doi: 10.1021/jp4115699

Auteurs

İbrahim Hanif Nazlı (İH)

Department of Chemistry, Graduate School of Natural and Applied Science, Dokuz Eylul University, Buca, 35160, Izmir, Turkey.
Department of Chemistry, Faculty of Sciences, Izmir Institute of Technology, Urla, 35430, Izmir, Turkey.

Gül Yakalı (G)

Department of Engineering Sciences, Faculty of Engineering, Izmir Katip Celebi University, Cigli, 35620, İzmir, Turkey. gul_ozkan13@hotmail.com.

Derya Topkaya (D)

Department of Chemistry, Faculty of Sciences, Dokuz Eylul University, Buca, 35160, Izmir, Turkey.

Merve İzmirli (M)

Department of Chemistry, Graduate School of Natural and Applied Science, Dokuz Eylul University, Buca, 35160, Izmir, Turkey.

Sema Demirci Uzun (SD)

Department of Engineering Sciences, Faculty of Engineering, Izmir Katip Celebi University, Cigli, 35620, İzmir, Turkey.

Serap Alp (S)

Department of Chemistry, Faculty of Sciences, Dokuz Eylul University, Buca, 35160, Izmir, Turkey.

Classifications MeSH