{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,18]],"date-time":"2026-03-18T10:10:20Z","timestamp":1773828620827,"version":"3.50.1"},"reference-count":45,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2022,3,16]],"date-time":"2022-03-16T00:00:00Z","timestamp":1647388800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21805049 and 22074025"],"award-info":[{"award-number":["21805049 and 22074025"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100010256","name":"Guangzhou Municipal Science and Technology Project","doi-asserted-by":"publisher","award":["202102010426 and 202102010473"],"award-info":[{"award-number":["202102010426 and 202102010473"]}],"id":[{"id":"10.13039\/501100010256","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>Six nonlinear, optical chromophores, Z1\u2013Z6, based on the bis(N,N-diethyl)aniline-derived donor and thiolated isophorone bridge, were designed and synthesized. The bis(N,N-diethyl)aniline-derived donor was applied in a chromophore with thiolated isophorone as an electron bridge for the first time. In particular, the bridge parts of chromophores Z2\u2013Z6 were modified with different functional groups, including tert-butyltrimethylsilane and tert-butyl(methyl)diphenylsilane derivative: 1,3-bis(trifluoromethyl)benzene and alkylaniline cyanoacetate, respectively. Density functional theory calculations suggested this series of chromophores show much greater hyperpolarizability than traditional, nonlinear, optical chromophores due to strong electron donor ability. These chromophores, Z1\u2013Z6, showed very high poling efficiencies due to the large steric hindrance and hyperpolarizability of the chromophores. A large poling efficiency (2.04 \u00b1 0.08 nm2\/V2) and r33 value (193 pm\/V) were achieved for polymeric thin films doped with 25 wt% chromophore Z6 at 1310 nm.<\/jats:p>","DOI":"10.3390\/sym14030586","type":"journal-article","created":{"date-parts":[[2022,3,16]],"date-time":"2022-03-16T22:15:04Z","timestamp":1647468904000},"page":"586","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Synthesis of Bis(N,N-diethyl)aniline-Based, Nonlinear, Optical Chromophores with Increased Electro-Optic Activity by Optimizing the Thiolated Isophorone Bridge"],"prefix":"10.3390","volume":"14","author":[{"given":"Xiaoqing","family":"Huang","sequence":"first","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ziheng","family":"Li","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Meishan","family":"Peng","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ziying","family":"Zeng","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zeling","family":"Huang","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3757-4692","authenticated-orcid":false,"given":"Fenggang","family":"Liu","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xunyu","family":"Chen","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zhiwei","family":"Liang","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jiahai","family":"Wang","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,3,16]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"056106","DOI":"10.1063\/1.5086868","article-title":"500 GHz plasmonic Mach-Zehnder modulator enabling sub-THz microwave photonics","volume":"4","author":"Burla","year":"2019","journal-title":"Apl. Photonics."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1021\/cr9000429","article-title":"Electric Field Poled Organic Electro-optic Materials: State of the Art and Future Prospects","volume":"110","author":"Dalton","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"860","DOI":"10.1126\/science.aay8645","article-title":"Nano-opto-electro-mechanical switches operated at CMOS-level voltages","volume":"366","author":"Haffner","year":"2019","journal-title":"Science"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"338","DOI":"10.1038\/s41928-020-0417-9","article-title":"A monolithic bipolar CMOS electronic-plasmonic high-speed transmitter","volume":"3","author":"Koch","year":"2020","journal-title":"Nat. Electron."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"5550","DOI":"10.1038\/s41467-019-13490-x","article-title":"Compact and ultra-efficient broadband plasmonic terahertz field detector","volume":"10","author":"Salamin","year":"2019","journal-title":"Nat. Commun."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"16823","DOI":"10.1364\/OE.27.016823","article-title":"120 GBd plasmonic Mach-Zehnder modulator with a novel differential electrode design operated at a peak-to-peak drive voltage of 178 mV","volume":"27","author":"Baeuerle","year":"2019","journal-title":"Opt. Express"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1901921","DOI":"10.1002\/adom.201901921","article-title":"X-Shaped Alignment of Chromophores: Potential Alternative for Efficient Organic Terahertz Generators","volume":"8","author":"Lee","year":"2020","journal-title":"Adv. Opt. Mater."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"118","DOI":"10.1007\/s10118-019-2307-z","article-title":"Dendronized Polymers with High FTC-chromophore Loading Density: Large Second-order Nonlinear Optical Effects, Good Temporal and Thermal Stability","volume":"38","author":"Jin","year":"2020","journal-title":"Chin. J. Polym. Sci."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1016\/j.dyepig.2015.05.003","article-title":"Comparative studies on structure-nonlinearity relationships in a series of novel second-order nonlinear optical chromophores with different aromatic amine donors","volume":"120","author":"Liu","year":"2015","journal-title":"Dyes Pigments"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"3119","DOI":"10.1039\/C6TC00358C","article-title":"Structure-function relationship exploration for enhanced thermal stability and electro-optic activity in monolithic organic NLO chromophores","volume":"4","author":"Jin","year":"2016","journal-title":"J. Mater. Chem. C"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"3258","DOI":"10.1021\/ar5000727","article-title":"Optimizing Calculations of Electronic Excitations and Relative Hyperpolarizabilities of Electrooptic Chromophores","volume":"47","author":"Johnson","year":"2014","journal-title":"Acc. Chem. Res."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"109423","DOI":"10.1016\/j.dyepig.2021.109423","article-title":"Design and synthesis of Phenylaminothiophene donor-based chromophore with enhanced electro-optic activity","volume":"192","author":"Yang","year":"2021","journal-title":"Dyes. Pigments."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"9226","DOI":"10.1039\/D0TC01845G","article-title":"Synthesis of nonlinear optical chromophores with isophorone-derived bridges for enhanced thermal stability and electro-optic activity","volume":"8","author":"Liu","year":"2020","journal-title":"J. Mater. Chem. C"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3425","DOI":"10.1021\/cm800054y","article-title":"Site-isolated electro-optic chromophores based on substituted 2,2 \u2032-bis(3,4-propylenedioxythiophene) pi-conjugated bridges","volume":"20","author":"Hammond","year":"2008","journal-title":"Chem. Mater."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"4471","DOI":"10.1021\/ol701814r","article-title":"Phenyltetraene-based nonlinear optical chromophores with enhanced chemical stability and electrooptic activity","volume":"9","author":"Luo","year":"2007","journal-title":"Org. Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2840","DOI":"10.1039\/C8TC00083B","article-title":"Design, synthesis, and properties of nonlinear optical chromophores based on a verbenone bridge with a novel dendritic acceptor","volume":"6","author":"Sun","year":"2018","journal-title":"J. Mater. Chem. C"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2982","DOI":"10.1021\/cm052861i","article-title":"Pyrroline chromophores for electro-optics","volume":"18","author":"Jang","year":"2006","journal-title":"Chem. Mater."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2393","DOI":"10.1021\/cm011734t","article-title":"alpha-Hydroxy ketone precursors leading to a novel class of electro-optic acceptors","volume":"14","author":"He","year":"2002","journal-title":"Chem. Mater."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"15009","DOI":"10.1039\/D0TC03224G","article-title":"High-performance organic second- and third-order nonlinear optical materials for ultrafast information processing","volume":"8","author":"Wu","year":"2020","journal-title":"J. Mater. Chem. C"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1374","DOI":"10.1039\/C8QM00128F","article-title":"Janus molecules: Large second-order nonlinear optical performance, good temporal stability, excellent thermal stability and spherical structure with optimized dendrimer structure","volume":"2","author":"Chen","year":"2018","journal-title":"Mater. Chem. Front."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1002\/tcr.201600065","article-title":"Second-Order Nonlinear Optical Dendrimers and Dendronized Hyperbranched Polymers","volume":"17","author":"Tang","year":"2017","journal-title":"Chem. Rec."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1039\/C9QM00508K","article-title":"Self-assembled binary multichromophore dendrimers with enhanced electro-optic coefficients and alignment stability","volume":"4","author":"Xu","year":"2020","journal-title":"Mater. Chem. Front."},{"key":"ref_23","first-page":"155","article-title":"Recent Advances in Second Order Nonlinear Optical Polymers with Dendritic Structure","volume":"2","author":"Li","year":"2017","journal-title":"Acta Polym. Sin."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"4016","DOI":"10.1039\/C6PY00546B","article-title":"A series of dendronized hyperbranched polymers with dendritic chromophore moieties in the periphery: Convenient synthesis and large nonlinear optical effects","volume":"7","author":"Yang","year":"2016","journal-title":"Polym. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"4012","DOI":"10.1021\/acs.macromol.0c00563","article-title":"A Correlation Study between Dendritic Structure and Macroscopic Nonlinearity for Second-Order Nonlinear Optical Materials","volume":"53","author":"Zang","year":"2020","journal-title":"Macromolecules"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"5047","DOI":"10.1021\/cm801097k","article-title":"Donor-acceptor thiolated polyenic chromophores exhibiting large optical nonlinearity and excellent photostability","volume":"20","author":"Cheng","year":"2008","journal-title":"Chem. Mater."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"108751","DOI":"10.1016\/j.dyepig.2020.108751","article-title":"Enhanced thermal stability and electro-optic activity from fluorene-based nonlinear optical chromophores","volume":"183","author":"Liu","year":"2020","journal-title":"Dyes Pigments"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"263","DOI":"10.1007\/s11426-020-9860-5","article-title":"Systematic study of the structure-property relationship of a series of near-infrared absorbing push-pull heptamethine chromophores for electro-optics","volume":"64","author":"Zhang","year":"2021","journal-title":"Sci. China-Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5776","DOI":"10.1039\/C4CP05829A","article-title":"The synthesis of new double-donor chromophores with excellent electro-optic activity by introducing modified bridges","volume":"17","author":"Yang","year":"2015","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"6704","DOI":"10.1039\/C7TC01175J","article-title":"Enhancement of electro-optic properties of bis(N,N-diethyl)aniline based second order nonlinear chromophores by introducing a stronger electron acceptor and modifying the \u03c0-bridge","volume":"5","author":"Zhang","year":"2017","journal-title":"J. Mater. Chem. C"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"11423","DOI":"10.1039\/C5TC02764K","article-title":"Synthesis and optical nonlinear properties of novel Y-shaped chromophores with excellent electro-optic activity","volume":"3","author":"Yang","year":"2015","journal-title":"J. Mater. Chem. C"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"8341","DOI":"10.1039\/D1QM01337H","article-title":"Design and synthesis of organic optical nonlinear multichromophore dendrimers based on double-donor structures","volume":"5","author":"Liu","year":"2021","journal-title":"Mater. Chem. Front."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"5494","DOI":"10.1039\/D0TC00332H","article-title":"The synthesis of second-order nonlinear optical chromophores with conjugated steric hindrance for electro-optics at 850 nm","volume":"8","author":"Wu","year":"2020","journal-title":"J. Mater. Chem. C"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"29679","DOI":"10.1039\/C5CP04959H","article-title":"Nonlinear optical chromophores based on Dewar\u2019s rules: Enhancement of electro-optic activity by introducing heteroatoms into the donor or bridge","volume":"17","author":"Xu","year":"2015","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3043","DOI":"10.1021\/cm010463j","article-title":"Low V-pi electrooptic modulators from CLD-1: Chromophore design and synthesis, material processing, and characterization","volume":"13","author":"Zhang","year":"2001","journal-title":"Chem. Mater."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"5873","DOI":"10.1016\/j.tetlet.2010.08.060","article-title":"Effect of modified donor units on molecular hyperpolarizability of thienyl-vinylene nonlinear optical chromophores","volume":"51","author":"Zhang","year":"2010","journal-title":"Tetrahedron Lett."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"7785","DOI":"10.1039\/C4TC00900B","article-title":"Nonlinear optical chromophores containing a novel pyrrole-based bridge: Optimization of electro-optic activity and thermal stability by modifying the bridge","volume":"2","author":"Liu","year":"2014","journal-title":"J. Mater. Chem. C"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"8019","DOI":"10.1039\/C9TC01658A","article-title":"Synthesis of novel nonlinear optical chromophores with enhanced electro-optic activity by introducing suitable isolation groups into the donor and bridge","volume":"7","author":"Liu","year":"2019","journal-title":"J. Mater. Chem. C"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"4669","DOI":"10.1021\/cm0204066","article-title":"Synthesis of chromophores with extremely high electro-optic activities. 2. Isophorone- and combined isophorone-thiophene-based chromophores","volume":"14","author":"He","year":"2002","journal-title":"Chem. Mater."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"4662","DOI":"10.1021\/cm020405d","article-title":"Synthesis of chromophores with extremely high electro-optic activity. 1. Thiophene-bridge-based chromophores","volume":"14","author":"He","year":"2002","journal-title":"Chem. Mater."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1021\/ma0011688","article-title":"Electric poling and relaxation of thermoset polyurethane second-order nonlinear optical materials: Role of cross-linking and monomer rigidity","volume":"34","author":"Zhang","year":"2001","journal-title":"Macromolecules"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.dyepig.2018.04.036","article-title":"Structure-function relationship exploration for enhanced electro-optic activity in isophorone-based organic NLO chromophores","volume":"157","author":"Liu","year":"2018","journal-title":"Dyes and Pigments"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"127771","DOI":"10.1016\/j.molstruc.2020.127771","article-title":"Sensitizers for DSSC containing triazole motif with acceptor\/donor substituents - Correlation between theoretical and experimental data in prediction of consistent photophysical parameters","volume":"1207","author":"Zych","year":"2020","journal-title":"J. Mol. Struct."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1016\/j.commatsci.2019.04.041","article-title":"Is it worthwhile to deal with 1,3-disubstituted pyrene derivatives? - Photophysical, optical and theoretical study of substitution position effect of pyrenes containing tetrazole groups","volume":"165","author":"Zych","year":"2019","journal-title":"Comput. Mater. Sci."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"8866","DOI":"10.1364\/OE.14.008866","article-title":"Analysis of multiple reflection effects in reflective measurements of electro-optic coefficients of poled polymers in multilayer structures","volume":"14","author":"Park","year":"2006","journal-title":"Opt. Express"}],"container-title":["Symmetry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-8994\/14\/3\/586\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T22:37:32Z","timestamp":1760135852000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-8994\/14\/3\/586"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,3,16]]},"references-count":45,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2022,3]]}},"alternative-id":["sym14030586"],"URL":"https:\/\/doi.org\/10.3390\/sym14030586","relation":{},"ISSN":["2073-8994"],"issn-type":[{"value":"2073-8994","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,3,16]]}}}