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An efficient two\u2010step synthesis allowed for a modular assembly of differently functionalized compounds. The dithieno[3,2\u2010<jats:italic>b<\/jats:italic>:2\u2032,3\u2032\u2010<jats:italic>d<\/jats:italic>]phosphole system exhibits extraordinary optoelectronic properties with respect to wavelength, intensity, and tunability. Owing to the nucleophilic nature of the central phosphorus atom, its significant electronic influence on the conjugated \u03c0 system can be altered selectively by chemically facile modifications such as oxidation or complexation with Lewis acids or transition metals. All the dithienophosphole species presented show very strong blue photoluminescence with excellent quantum yield efficiencies supporting their potential utility as blue\u2010light emitting components in organic light emitting diodes (OLEDs). Furthermore, depending on the electronic nature of the phosphorus center, the materials exhibit distinctive optoelectronic properties suggesting that the dithieno[3,2\u2010<jats:italic>b<\/jats:italic>:2\u2032,3\u2032\u2010<jats:italic>d<\/jats:italic>]phosphole system may be useful as sensory material. Theoretical calculations, including time\u2010dependent DFT methods, revealed the excellent predictability of the structures and optoelectronic properties of the functionalized dithienophospholes allowing the design of future dithieno[3,2\u2010<jats:italic>b<\/jats:italic>:2\u2032,3\u2032\u2010<jats:italic>d<\/jats:italic>]phosphole\u2010based materials to be \u201dstream\u2010lined\u201d. By using tin\u2010functionalized dithienophosphole monomers, a strategy, which involves Stille coupling, towards extended \u03c0\u2010conjugated materials with significantly redshifted optoelectronic properties is also presented.<\/jats:p>","DOI":"10.1002\/chem.200500152","type":"journal-article","created":{"date-parts":[[2005,5,25]],"date-time":"2005-05-25T04:48:55Z","timestamp":1116996535000},"page":"4687-4699","source":"Crossref","is-referenced-by-count":159,"title":["From Model Compounds to Extended \u03c0\u2010Conjugated Systems: Synthesis and Properties of Dithieno[3,2\u2010<i>b<\/i>:2\u2032,3\u2032\u2010<i>d<\/i>]phospholes"],"prefix":"10.1002","volume":"11","author":[{"given":"Thomas","family":"Baumgartner","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Werner","family":"Bergmans","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tam\u00e1s","family":"K\u00e1rp\u00e1ti","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Toni","family":"Neumann","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Nieger","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"L\u00e1szl\u00f3","family":"Nyul\u00e1szi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2005,7,25]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200200557"},{"key":"e_1_2_6_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200200557"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(02)01171-3"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja029120s"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200460939"},{"key":"e_1_2_6_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460939"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0394683"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20011001)7:19<4222::AID-CHEM4222>3.0.CO;2-3"},{"key":"e_1_2_6_8_2","unstructured":"See for example:"},{"key":"e_1_2_6_9_2","volume-title":"Handbook of Oligo\u2010 and Polythiophenes","year":"1998"},{"key":"e_1_2_6_10_2","volume-title":"Conjugated Conducting Polymers","year":"1992"},{"key":"e_1_2_6_11_2","unstructured":"G. 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