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The reaction yields and product stability were significantly affected by the identity of the diamine and anhydride substituents. On the other hand, the substituents of the benzimidazole ring allowed fine tuning of the emission maxima, fluorescence quantum yields, and redox potentials. The HOMO\u2013LUMO levels were estimated by cyclic voltammetry in film on indium tin oxide (ITO) and compared with values obtained by other methods. The described benzimidazoles showed high crystallinity, which is attributed to a high planarity and interactions between carbon and heteroatoms. These compounds showed n\u2010type semiconducting behavior in organic field\u2010effect transistors (OFETs). Optimized devices for fluorinated NTCBI (naphthalene tetracarboxylic bisbenzimidazole) showed respectable electron mobilities of \u223c10\n                    <jats:sup>\u22122<\/jats:sup>\n                    \u2005cm\n                    <jats:sup>2<\/jats:sup>\n                    \u2009V\n                    <jats:sup>\u22121<\/jats:sup>\n                    \u2009s\n                    <jats:sup>\u22121<\/jats:sup>\n                    .\n                  <\/jats:p>","DOI":"10.1002\/chem.201403058","type":"journal-article","created":{"date-parts":[[2014,7,30]],"date-time":"2014-07-30T17:20:29Z","timestamp":1406740829000},"page":"11835-11846","source":"Crossref","is-referenced-by-count":71,"title":["Benzimidazole Derivatives: Synthesis, Physical Properties, and n\u2010Type Semiconducting Properties"],"prefix":"10.1002","volume":"20","author":[{"given":"Masashi","family":"Mamada","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"C\u00e9sar","family":"P\u00e9rez\u2010Bol\u00edvar","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daisuke","family":"Kumaki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nina A.","family":"Esipenko","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shizuo","family":"Tokito","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"suffix":"Jr.","given":"Pavel","family":"Anzenbacher","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,7,30]]},"reference":[{"key":"e_1_2_6_1_2","volume-title":"Industrial Organic Pigments","author":"Herbst M.","year":"1993"},{"key":"e_1_2_6_2_2","unstructured":"\u00a0"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.1995199507164"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm990051z"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0143-7208(03)00083-4"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.257.5066.63"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1038\/23912"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200306102"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja000219d"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100199a032"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2614(93)85142-B"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm034140u"},{"key":"e_1_2_6_13_2","unstructured":"\u00a0"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200461324"},{"key":"e_1_2_6_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200461324"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200701478"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm102296d"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201001402"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100380z"},{"key":"e_1_2_6_19_2","unstructured":"\u00a0"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.293.5532.1119"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja071760d"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm1023019"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.96937"},{"key":"e_1_2_6_24_2","unstructured":"\u00a0"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.1829776"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.1871347"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.200900298"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.3598426"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100513"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.2890425"},{"key":"e_1_2_6_31_2","unstructured":"\u00a0"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-4095(20020304)14:5<371::AID-ADMA371>3.0.CO;2-5"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ica.2007.02.047"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.sna.2010.05.030"},{"key":"e_1_2_6_35_2","unstructured":"\u00a0"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1038\/35006603"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja000870g"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm0704579"},{"key":"e_1_2_6_39_2","first-page":"3715","volume":"19","author":"Kr\u00fcger H.","year":"2007","journal-title":"Adv. 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