{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T05:16:13Z","timestamp":1789967773653,"version":"4.0.1"},"reference-count":81,"publisher":"American Chemical Society (ACS)","issue":"34","license":[{"start":{"date-parts":[[2016,5,4]],"date-time":"2016-05-04T00:00:00Z","timestamp":1462320000000},"content-version":"vor","delay-in-days":1009,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2013,8,28]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>9,10-Dihydro-9,10-diboraanthracene (DBA) provides a versatile scaffold for the development of boron-doped organic luminophores. Symmetrically C-halogenated DBAs are obtained through the condensation of 4-bromo-1,2-bis(trimethylsilyl)benzene or 4,5-dichloro-1,2-bis(trimethylsilyl)benzene with BBr3 in hexane. Unsymmetrically C-halogenated DBAs are formed via an electrophilic solvent activation reaction if the synthesis is carried out in o-xylene. Mechanistic insight has been achieved by in situ NMR spectroscopy, which revealed C-halogenated 1,2-bis(dibromoboryl)benzenes to be the key intermediates. Treatment of the primary 9,10-dibromo-DBAs with MesMgBr yields air- and water-stable C-halogenated 9,10-dimesityl-DBAs (2-Br-6,7-Me2-DBA(Mes)2; 2,6-Br2-DBA(Mes)2; 2,3-Cl2-6,7-Me2-DBA(Mes)2; 2,3,6,7-Cl4-DBA(Mes)2). Subsequent Stille-type C\u2013C-coupling reactions give access to corresponding phenyl, 2-thienyl, and p-N,N-diphenylaminophenyl derivatives, which act as highly emissive donor\u2013acceptor dyads or donor\u2013acceptor\u2013donor triads both in solution and in the solid state. 2-Thienyl was chosen as a model substituent to show that already a variation of the number and\/or the positional distribution of the donor groups suffices to tune the emission wavelength of the resulting benchtop stable compounds from 469 nm (blue) to 540 nm (green). A further shift of the fluorescence maximum to 594 nm (red) can be achieved by switching from 2-thienyl to p-aminophenyl groups. A comparison of the optoelectronic properties of selected C-substituted DBA(Mes)2 derivatives with those of the isostructural anthracene analogues unveiled the following: (i) The DBA core is a much better electron acceptor. (ii) The emission colors of DBAs fall in the visible range of the spectrum (blue to orange), while anthracenes emit exclusively in the near-ultraviolet to blue wavelength regime. (iii) DBAs show significantly higher solid-state quantum yields.<\/jats:p>","DOI":"10.1021\/ja406766e","type":"journal-article","created":{"date-parts":[[2013,7,30]],"date-time":"2013-07-30T13:51:34Z","timestamp":1375192294000},"page":"12892-12907","source":"Crossref","is-referenced-by-count":159,"title":["C-Functionalized, Air- and Water-Stable 9,10-Dihydro-9,10-diboraanthracenes: Efficient Blue to Red Emitting Luminophores"],"prefix":"10.1021","volume":"135","author":[{"given":"Christian","family":"Reus","sequence":"first","affiliation":[{"name":"J. W. Goethe-Universita\u0308t Frankfurt Institut fu\u0308r Anorganische und Analytische Chemie, , Max-von-Laue-Stra\u00dfe 7, D-60438 Frankfurt (Main), Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sabine","family":"Weidlich","sequence":"additional","affiliation":[{"name":"J. W. Goethe-Universita\u0308t Frankfurt Institut fu\u0308r Anorganische und Analytische Chemie, , Max-von-Laue-Stra\u00dfe 7, D-60438 Frankfurt (Main), Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Bolte","sequence":"additional","affiliation":[{"name":"J. W. Goethe-Universita\u0308t Frankfurt Institut fu\u0308r Anorganische und Analytische Chemie, , Max-von-Laue-Stra\u00dfe 7, D-60438 Frankfurt (Main), Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hans-Wolfram","family":"Lerner","sequence":"additional","affiliation":[{"name":"J. W. 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