{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,30]],"date-time":"2026-06-30T20:17:08Z","timestamp":1782850628439,"version":"3.54.5"},"reference-count":47,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2015,1,28]],"date-time":"2015-01-28T00:00:00Z","timestamp":1422403200000},"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":[[2015,3,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The systematic synthesis and photophysical, electrochemical and computational studies on an extended series of triphenylamine\u2010[C\uf8fdC\u20101,4\u2010C<jats:sub>6<\/jats:sub>H<jats:sub>2<\/jats:sub>(OR)<jats:sub>2<\/jats:sub>]<jats:sub><jats:italic>n<\/jats:italic><\/jats:sub>\u2010C\uf8fdC\u2010diphenyl\u20101,3,4\u2010oxadiazole dyad molecules (the OR groups are at 2,5\u2010positions of the <jats:italic>para<\/jats:italic>\u2010phenylene ring and R=C<jats:sub>6<\/jats:sub>H<jats:sub>13<\/jats:sub>; <jats:italic>n<\/jats:italic>=0\u20135, compounds <jats:bold>1<\/jats:bold>, <jats:bold>2<\/jats:bold>, <jats:bold>3<\/jats:bold>, <jats:bold>4<\/jats:bold> and <jats:bold>5<\/jats:bold>, respectively) are reported. Related molecules with identical end groups, triphenylamine\u2010C\uf8fdC\u20101,4\u2010C<jats:sub>6<\/jats:sub>H<jats:sub>2<\/jats:sub>(OR)<jats:sub>2<\/jats:sub>\u2010C\uf8fdC\u2010triphenylamine (R=C<jats:sub>6<\/jats:sub>H<jats:sub>13<\/jats:sub>; <jats:bold>6<\/jats:bold>) and diphenyl\u20101,3,4\u2010oxadiazole\u2010[C\uf8fdC\u2010C<jats:sub>6<\/jats:sub>H<jats:sub>2<\/jats:sub>(OR)<jats:sub>2<\/jats:sub>]<jats:sub>2<\/jats:sub>\u2010C\uf8fdC\u2010diphenyl\u20101,3,4\u2010oxadiazole (R=C<jats:sub>6<\/jats:sub>H<jats:sub>13<\/jats:sub>; <jats:bold>7<\/jats:bold>) were also studied. These D\u2013B\u2013A <jats:bold>1<\/jats:bold>\u2013<jats:bold>5<\/jats:bold>, D\u2013B\u2013D <jats:bold>6<\/jats:bold> and A\u2013B\u2013A <jats:bold>7<\/jats:bold> (D=electron donor, B=bridge, A=electron acceptor) systems were synthesized using palladium\u2010catalysed cross\u2010coupling reactions of new <jats:italic>p<\/jats:italic>\u2010phenyleneethynylene building blocks. Steady\u2010state emission studies on the dyads <jats:bold>1<\/jats:bold>\u2013<jats:bold>5<\/jats:bold> reveal a complicated behavior of the emission that is strongly medium dependent. In low polarity solvents the emission is characterized by a sharp high\u2010energy peak attributed to fluorescence from a locally excited (LE) state. In more polar environments the LE state is effectively quenched by transfer into an intramolecular charge\u2010transfer (ICT) state. The medium dependence is also observed in the quantum yields (QYs) which are high in cyclohexane and low in acetonitrile, thus also indicating charge\u2010transfer character. Low\u2010temperature emission spectra for <jats:bold>2<\/jats:bold>\u2013<jats:bold>5<\/jats:bold> in dichloromethane and diethyl ether also reveal two distinct excited states, namely the LE state and the conventional ICT state, depending on solvent and temperature. Hybrid DFT calculations for <jats:bold>1<\/jats:bold>\u2013<jats:bold>7<\/jats:bold> establish that the OPE bridge is involved in both frontier orbitals where the bridge character increases as the bridge length increases. Computed TD\u2010DFT data on <jats:bold>1<\/jats:bold>\u2013<jats:bold>5<\/jats:bold> assign the emission maxima in cyclohexane as LE transitions. Each time\u2010resolved emission measurement on <jats:bold>2<\/jats:bold>\u2013<jats:bold>7<\/jats:bold> in cyclohexane and diethyl ether reveals a wavelength dependent bi\u2010exponential decay of the emission with a fast component in the 5\u201361\u2005ps range on blue detection and a slower approximately 1\u2005ns phase, independent of detection wavelength. The fast component is attributed to LE fluorescence and this emission component is rate limited and quenched by transfer into an ICT state. The fast LE fluorescence component varies systematically with conjugation length for the series of D\u2013B\u2013A dyads <jats:bold>2<\/jats:bold>\u2013<jats:bold>5<\/jats:bold>. An attenuation factor <jats:italic>\u03b2<\/jats:italic> of 0.15\u2005\u00c5<jats:sup>\u22121<\/jats:sup> was determined in accordance with an ICT superexchange mechanism.<\/jats:p>","DOI":"10.1002\/chem.201406080","type":"journal-article","created":{"date-parts":[[2015,1,28]],"date-time":"2015-01-28T11:45:57Z","timestamp":1422445557000},"page":"3997-4007","source":"Crossref","is-referenced-by-count":38,"title":["Oligo(<i>p<\/i>\u2010phenyleneethynylene) (OPE) Molecular Wires: Synthesis and Length Dependence of Photoinduced Charge Transfer in OPEs with Triarylamine and Diaryloxadiazole End Groups"],"prefix":"10.1002","volume":"21","author":[{"given":"Katharine E.","family":"Linton","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mark A.","family":"Fox","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lars\u2010Olof","family":"P\u00e5lsson","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin R.","family":"Bryce","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,1,28]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1007\/b136066"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1007\/b136068"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp0268462"},{"key":"e_1_2_6_4_2","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","unstructured":"M. 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