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Restricted bond rotation of the phenoxy fragments leads to dyes <jats:bold>2<\/jats:bold> and <jats:bold>3<\/jats:bold>, which absorb and fluoresce more intensely at longer wavelengths relative to the unconstrained dye <jats:bold>1<\/jats:bold>. Reduction of the conformational flexibility in <jats:bold>2<\/jats:bold> and <jats:bold>3<\/jats:bold> leads to significantly higher fluorescence quantum yields compared to those of <jats:bold>1<\/jats:bold>. X\u2010ray diffraction analysis shows the progressively more extended planarity of the chromophore in line with the increasing conformational restriction in the series <jats:bold>1<\/jats:bold>\u2192<jats:bold>2<\/jats:bold>\u2192<jats:bold>3<\/jats:bold>, which explains the larger red shifts of the absorption and emission spectra. These conclusions are confirmed by quantum chemical calculations of the lowest electronic excitations in <jats:bold>1<\/jats:bold>, <jats:bold>1a<\/jats:bold>, <jats:bold>2<\/jats:bold>, <jats:bold>2a<\/jats:bold>, <jats:bold>3<\/jats:bold> and dyes of related chemical structures. The effect of the molecular structure on the visible absorption and fluorescence emission properties of <jats:bold>1<\/jats:bold>, <jats:bold>1a<\/jats:bold>, <jats:bold>2<\/jats:bold>, <jats:bold>2a<\/jats:bold>, <jats:bold>3<\/jats:bold> has been examined as a function of solvent by means of the new, generalized treatment of the solvent effect (<jats:italic>J. Phys. Chem. B<\/jats:italic> <jats:bold>2009<\/jats:bold>, <jats:italic>113<\/jats:italic>, 5951\u20135960). Solvent polarizability is the primary factor responsible for the small solvent\u2010dependent shifts of the visible absorption and fluorescence emission bands of these dyes.<\/jats:p>","DOI":"10.1002\/asia.201000248","type":"journal-article","created":{"date-parts":[[2010,8,10]],"date-time":"2010-08-10T05:56:43Z","timestamp":1281419803000},"page":"2016-2026","source":"Crossref","is-referenced-by-count":53,"title":["Synthesis, Spectroscopy, Crystal Structure Determination, and Quantum Chemical Calculations of BODIPY Dyes with Increasing Conformational Restriction and Concomitant Red\u2010Shifted Visible Absorption and Fluorescence Spectra"],"prefix":"10.1002","volume":"5","author":[{"given":"Volker","family":"Leen","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenwu","family":"Qin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wensheng","family":"Yang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jie","family":"Cui","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chan","family":"Xu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoliang","family":"Tang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weisheng","family":"Liu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Koen","family":"Robeyns","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luc","family":"Van\u2005Meervelt","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David","family":"Beljonne","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roberto","family":"Lazzaroni","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claire","family":"Tonnel\u00e9","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"No\u00ebl","family":"Boens","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wim","family":"Dehaen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2010,8,30]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19687180119"},{"key":"e_1_2_6_2_2","unstructured":"\u00a0"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr078381n"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200702070"},{"key":"e_1_2_6_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702070"},{"key":"e_1_2_6_5_2","volume-title":"The Handbook. 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