{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,26]],"date-time":"2026-06-26T04:14:01Z","timestamp":1782447241687,"version":"3.54.5"},"reference-count":95,"publisher":"Wiley","issue":"38","license":[{"start":{"date-parts":[[2012,8,14]],"date-time":"2012-08-14T00:00:00Z","timestamp":1344902400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2012,9,17]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A new series of 2,1,3\u2010benzothiadiazole (BT) acceptors with different conjugated aryl\u2010vinylene side chains have been designed and used to build efficient low\u2010bandgap (LBG) photovoltaic copolymers. Based on benzo[1,2\u2010<jats:italic>b<\/jats:italic>:3,4\u2010<jats:italic>b<\/jats:italic>\u2032]dithiophene and the resulting new BT derivatives, three two\u2010dimensional (2D)\u2010like donor (D)\u2013acceptor (A) conjugated copolymers have been synthesised by Stille coupling polymerisation. These copolymers were characterised by NMR spectroscopy, gel\u2010permeation chromatography, thermogravimetric analysis and differential scanning calorimetry. UV\/Vis absorption and cyclic voltammetry measurements indicated that their optical and electrochemical properties can be facilely modified by changing the structures of the conjugated aryl\u2010vinylene side chains. The copolymer with phenyl\u2010vinylene side chains exhibited the best light harvesting and smallest bandgap of the three copolymers. The basic electronic structures of D\u2013A model compounds of these copolymers were also studied by DFT calculations at the B3LYP\/6\u201031G* level of theory. Polymer solar cells (PSCs) with a typical structure of indium tin oxide (ITO)\/poly(3,4\u2010ethylenedioxythiophene) (PEDOT):poly(styrenesulfonate) (PSS)\/copolymer:[6,6]\u2010phenyl\u2010C<jats:sub>61<\/jats:sub>(C<jats:sub>71<\/jats:sub>)\u2010butyric acid\u2010methyl ester (PCBM)\/calcium (Ca)\/aluminum (Al) were fabricated and measured under the illumination of AM1.5G at 100\u2005mW\u2009cm<jats:sup>\u22122<\/jats:sup>. The results showed that the device based on the copolymer with phenyl\u2010vinylene side chains had the highest efficiency of 2.17\u2009% with PC<jats:sub>71<\/jats:sub>BM as acceptor. The results presented herein indicate that all the prepared copolymers are promising candidates for roll\u2010to\u2010roll manufacturing of efficient PSCs. Suitable electronic, optical and photovoltaic properties of BT\u2010based copolymers can also be achieved by fine\u2010tuning the structures of the aryl\u2010vinylene side chains for photovoltaic application.<\/jats:p>","DOI":"10.1002\/chem.201200730","type":"journal-article","created":{"date-parts":[[2012,8,14]],"date-time":"2012-08-14T07:26:50Z","timestamp":1344929210000},"page":"12140-12151","source":"Crossref","is-referenced-by-count":43,"title":["Synthesis and Photovoltaic Properties of Two\u2010Dimensional Low\u2010Bandgap Copolymers Based on New Benzothiadiazole Derivatives with Different Conjugated Arylvinylene Side Chains"],"prefix":"10.1002","volume":"18","author":[{"given":"Qiang","family":"Peng","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Siew\u2010Lay","family":"Lim","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ivy Hoi\u2010Ka","family":"Wong","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jun","family":"Xu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhi\u2010Kuan","family":"Chen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2012,8,14]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr050149z"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200702506"},{"key":"e_1_2_6_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702506"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1141711"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/b823001c"},{"key":"e_1_2_6_6_2","unstructured":"\u00a0"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1038\/nphoton.2009.192"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1038\/nphoton.2009.69"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0jm01178a"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201101933"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.332.6027.293"},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.200500211"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1038\/nmat1500"},{"key":"e_1_2_6_15_2","unstructured":"\u00a0"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200800606"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar900061z"},{"key":"e_1_2_6_18_2","unstructured":"\u00a0"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr950257t"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.403"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200902469"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1jm10433k"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma201648t"},{"key":"e_1_2_6_24_2","unstructured":"\u00a0"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200700557"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm100661z"},{"key":"e_1_2_6_27_2","unstructured":"\u00a0"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200903528"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201005451"},{"key":"e_1_2_6_29_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201005451"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103782"},{"key":"e_1_2_6_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103782"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103313"},{"key":"e_1_2_6_31_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103313"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1ee01072g"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201103006"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja200314m"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1112595"},{"key":"e_1_2_6_36_2","unstructured":"\u00a0"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma051883n"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja060141m"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma071402v"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma062633p"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.synthmet.2008.08.010"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/macp.200900641"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp803187u"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.200700423"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200802379"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9066139"},{"key":"e_1_2_6_47_2","unstructured":"\u00a0"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma100616f"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm1027157"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma101491c"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/pola.24311"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/pola.24389"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/pola.24568"},{"key":"e_1_2_6_54_2","unstructured":"\u00a0"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar900073s"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar900065j"},{"key":"e_1_2_6_57_2","unstructured":"\u00a0"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200900510"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200304150"},{"key":"e_1_2_6_60_2","unstructured":"\u00a0"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.2836266"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/marc.200700470"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200602496"},{"key":"e_1_2_6_64_2","unstructured":"\u00a0"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1039\/b912258c"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma802720n"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1039\/b811031j"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma900601y"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma802052w"},{"key":"e_1_2_6_70_2","unstructured":"\u00a0"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma800820r"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200906934"},{"key":"e_1_2_6_72_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200906934"},{"key":"e_1_2_6_73_2","unstructured":"\u00a0"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma0100448"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma061861g"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp7105428"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.200390011"},{"key":"e_1_2_6_78_2","unstructured":"\u00a0"},{"key":"e_1_2_6_79_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0379-6779(99)00007-7"},{"key":"e_1_2_6_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma050378n"},{"key":"e_1_2_6_81_2","volume-title":"Density Functional Theory of Atoms and Molecules","author":"Parr R. G.","year":"1989"},{"key":"e_1_2_6_82_2","unstructured":"Gaussian\u200509 Revision\u2005A.2 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone B. Mennucci G.\u2005A. Petersson H. Nakatsuji M. Caricato X. Li H.\u2005P. Hratchian A.\u2005F. Izmaylov J. Bloino G. Zheng J.\u2005L. Sonnenberg M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven J.\u2005A. Montgomery Jr. J.\u2005E. Peralta F. Ogliaro M. Bearpark J.\u2005J. Heyd E. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov R. Kobayashi J. Normand K. Raghavachari A. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi N. Rega J.\u2005M. Millam M. Klene J.\u2005E. Knox J.\u2005B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R.\u2005E. Stratmann O. Yazyev A.\u2005J. Austin R. Cammi C. Pomelli J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma V.\u2005G. Zakrzewski G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg S. Dapprich A.\u2005D. Daniels \u00d6. Farkas J.\u2005B. Foresman J.\u2005V. Ortiz J. Cioslowski D.\u2005J. Fox Gaussian Inc. Wallingford CT 2009."},{"key":"e_1_2_6_83_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.3059554"},{"key":"e_1_2_6_84_2","unstructured":"\u00a0"},{"key":"e_1_2_6_85_2","doi-asserted-by":"publisher","DOI":"10.1002\/1616-3028(200110)11:5<374::AID-ADFM374>3.0.CO;2-W"},{"key":"e_1_2_6_86_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200501717"},{"key":"e_1_2_6_87_2","doi-asserted-by":"publisher","DOI":"10.1038\/nmat1928"},{"key":"e_1_2_6_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/pola.24887"},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200351647"},{"key":"e_1_2_6_89_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200351647"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201200730","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201200730","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T20:32:38Z","timestamp":1760301158000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201200730"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,8,14]]},"references-count":95,"journal-issue":{"issue":"38","published-print":{"date-parts":[[2012,9,17]]}},"alternative-id":["10.1002\/chem.201200730"],"URL":"https:\/\/doi.org\/10.1002\/chem.201200730","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,8,14]]}}}