{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,17]],"date-time":"2026-09-17T05:34:04Z","timestamp":1789623244587,"version":"build-2803163510"},"reference-count":57,"publisher":"Wiley","issue":"13","license":[{"start":{"date-parts":[[2013,7,8]],"date-time":"2013-07-08T00:00:00Z","timestamp":1373241600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemPhysChem"],"published-print":{"date-parts":[[2013,9,16]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>On the basis of our previous communication concerning a new family of thiophene\u2010armed tetraazaanthracene molecules, we present a further intensive investigation on this class of compounds substituted with different alkyl chains and their self\u2010assembled two\u2010dimensional (2D) nanostructures. These tetraazaanthracene molecules with different alkyl chains were prepared in good yields using the synthetic strategy we developed. In addition to the expected typical <jats:italic>n<\/jats:italic>\u2010type character, one compound exhibited aggregation behavior upon electrochemical reduction. Moreover, all molecules in the neutral state showed a strong tendency to aggregate in a binary solvent, as confirmed by optical spectral measurements. To investigate such self\u2010assembly behavior, a phase\u2010transfer method with a dichloromethane\/methanol (2:3) binary solvent system was used to prepare the nanostructures. By means of atomic force microscopy, transmission electron microscopy, and X\u2010ray diffraction, we found that the morphology of assembled 2D sheet\u2010like structures could be adjusted by varying the alkyl chain. The weak interactions arising from the heteroatoms (N and S) in the conjugated backbones play a key role in the formation and stabilization of layered structures.<\/jats:p>","DOI":"10.1002\/cphc.201300444","type":"journal-article","created":{"date-parts":[[2013,7,8]],"date-time":"2013-07-08T12:27:52Z","timestamp":1373286472000},"page":"2954-2960","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Two\u2010Dimensional Nanostructures by the Assembly of <i>n<\/i>\u2010Type Tetraazaanthracene\u2010Based Conjugated Molecules"],"prefix":"10.1002","volume":"14","author":[{"given":"Chunyang","family":"He","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dongqing","family":"Wu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fan","family":"Zhang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Minzhao","family":"Xue","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaodong","family":"Zhuang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Feng","family":"Qiu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinliang","family":"Feng","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,7,8]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/nmat1849"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/b916418a"},{"key":"e_1_2_6_4_2","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1sc00251a"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/B514389F"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35179j"},{"key":"e_1_2_6_8_2","unstructured":"\u00a0"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.276.5311.384"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/B920623J"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja068250o"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1165429"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500980"},{"key":"e_1_2_6_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500980"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200305137"},{"key":"e_1_2_6_15_2","unstructured":"\u00a0"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201004245"},{"key":"e_1_2_6_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004245"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar200226d"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja048819q"},{"key":"e_1_2_6_19_2","unstructured":"\u00a0"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/B608593H"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar900218d"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol901127q"},{"key":"e_1_2_6_23_2","unstructured":"\u00a0"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200502442"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja075045f"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2nr11635a"},{"key":"e_1_2_6_27_2","unstructured":"\u00a0"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1jm12801a"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.293.5532.1119"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja901357h"},{"key":"e_1_2_6_31_2","unstructured":"\u00a0"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/B401630K"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200461324"},{"key":"e_1_2_6_33_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200461324"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/smll.200600381"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc00015f"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200802148"},{"key":"e_1_2_6_37_2","unstructured":"\u00a0"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja050783u"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200900101"},{"key":"e_1_2_6_39_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200900101"},{"key":"e_1_2_6_40_2","unstructured":"\u00a0"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol301202v"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm9900305"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200900079"},{"key":"e_1_2_6_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200900079"},{"key":"e_1_2_6_44_2","unstructured":"\u00a0"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol061711q"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0563152"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801404"},{"key":"e_1_2_6_47_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801404"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200600379"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2sc20871g"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/la102891p"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0383118"}],"container-title":["ChemPhysChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcphc.201300444","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cphc.201300444","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T13:47:06Z","timestamp":1760363226000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cphc.201300444"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,7,8]]},"references-count":57,"journal-issue":{"issue":"13","published-print":{"date-parts":[[2013,9,16]]}},"alternative-id":["10.1002\/cphc.201300444"],"URL":"https:\/\/doi.org\/10.1002\/cphc.201300444","archive":["Portico"],"relation":{},"ISSN":["1439-4235","1439-7641"],"issn-type":[{"value":"1439-4235","type":"print"},{"value":"1439-7641","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,7,8]]},"assertion":[{"value":"2013-05-06","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2013-07-08","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}