| Revision as of 18:25, 19 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 20:20, 27 July 2023 edit undoWidefox (talk | contribs)Autopatrolled, Extended confirmed users, Page movers, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers106,737 editsm →top: bold alt article name per MOS |
| (25 intermediate revisions by 18 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 416384309 |
|
|
|
| Watchedfields = changed |
|
|ImageFile=Periflanthene.png |
|
|
⚫ |
| verifiedrevid = 424894498 |
| ⚫ |
|ImageSize=200px |
|
|
|
| ImageFile = Diindenoperylene.svg |
| ⚫ |
|IUPACName=Diindenoperylene |
|
|
⚫ |
| ImageSize = 240px |
| ⚫ |
|OtherNames=Periflanthen; Periflanthene |
|
|
|
| ImageAlt = Skeletal formula |
|
|
| ImageFile1 = Diindenoperylene-3D-balls.png |
|
|
| ImageSize1 = 240 |
|
|
| ImageAlt1 = Ball-and-stick model |
|
⚫ |
| PIN=Diindenoperylene |
|
⚫ |
| OtherNames=Periflanthen; Periflanthene |
|
|Section1={{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| Abbreviations=DIP |
|
| Abbreviations=DIP |
|
|
| CASNo_Ref = {{cascite|correct|??}} |
|
| CASNo=188-94-3 |
|
| CASNo=188-94-3 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = TQA4WPL7Y8 |
|
| PubChem=96712 |
|
| PubChem=96712 |
|
| SMILES=C1=CC2=C3C=CC4=C5C=CC6=C7C=CC=CC7=C8C6=C5C(=C9C4=C3C(=C2C=C1)C=C9)C=C8 |
|
| SMILES=C1=CC2=C3C=CC4=C5C=CC6=C7C=CC=CC7=C8C6=C5C(=C9C4=C3C(=C2C=C1)C=C9)C=C8 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = 87318 |
|
|
| InChI = 1/C32H16/c1-2-6-18-17(5-1)21-9-13-25-27-15-11-23-19-7-3-4-8-20(19)24-12-16-28(32(27)30(23)24)26-14-10-22(18)29(21)31(25)26/h1-16H |
|
|
| InChIKey = BKMIWBZIQAAZBD-UHFFFAOYAB |
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChI = 1S/C32H16/c1-2-6-18-17(5-1)21-9-13-25-27-15-11-23-19-7-3-4-8-20(19)24-12-16-28(32(27)30(23)24)26-14-10-22(18)29(21)31(25)26/h1-16H |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = BKMIWBZIQAAZBD-UHFFFAOYSA-N |
|
}} |
|
}} |
|
|Section2={{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| C=32|H=16 |
|
| C=32 | H=16 |
|
| Appearance=Orange solid |
|
| Appearance=Orange solid |
|
| Density= |
|
| Density= |
| Line 22: |
Line 39: |
|
| MainHazards= |
|
| MainHazards= |
|
| FlashPt= |
|
| FlashPt= |
|
|
| AutoignitionPt = |
|
| Autoignition= |
|
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Diindenoperylene''' (DIP) is an ] which receives attention because of its potential application in ] (]s, ]s) and ] (] tags). DIP is a planar ] derivative with two ]-groups attached to opposite sides of the perylene core. Its ] is C<sub>32</sub>H<sub>16</sub>, the full chemical name is diindenoperylene. Its ] has been described.<ref>J. von Braun, G. Manz, in Deutsches Reichspatentamt, Berlin. (Germany, 1934).</ref><ref name=clar>E. Clar, Polycyclic hydrocarbons (Academic Press, London, New York, 1964), p. 2</ref> |
|
'''Diindenoperylene''' ('''DIP''') is an ] which receives attention because of its potential application in ] (]s, ]s) and ] (] tags). DIP is a planar ] derivative with two ]-groups attached to opposite sides of the perylene core. Its ] is C<sub>32</sub>H<sub>16</sub>, the full chemical name is diindenoperylene. Its ] has been described.<ref>J. von Braun, G. Manz, in Deutsches Reichspatentamt, Berlin. (Germany, 1934).</ref><ref name=clar>E. Clar, Polycyclic hydrocarbons (Academic Press, London, New York, 1964), p. 2</ref> |
|
|
|
|
|
|
== Properties and uses == |
|
The ] is 400.48 g/mol, the dimensions of the molecule in its plane are ~18.4×7 Å.<ref>{{cite journal|last1=Dürr|first1=A. C.|last2=Schreiber|first2=F.|last3=Münch|first3=M.|last4=Karl|first4=N.|last5=Krause|first5=B.|last6=Kruppa|first6=V.|last7=Dosch|first7=H.|title=High structural order in thin films of the organic semiconductor diindenoperylene|journal=Applied Physics Letters|volume=81|pages=2276|year=2002|doi=10.1063/1.1508436}}</ref> and its ] temperature is above 330 °C.<ref>A. C. Dürr, Ph.D. thesis, Universität Stuttgart (2002)</ref> It is non-polar and therefore only slightly ], for example in ]. |
|
The ] is 400.48 g/mol, the dimensions of the molecule in its plane are ~18.4×7 Å.<ref>{{cite journal|last1=Dürr|first1=A. C.|last2=Schreiber|first2=F.|last3=Münch|first3=M.|last4=Karl|first4=N.|last5=Krause|first5=B.|last6=Kruppa|first6=V.|last7=Dosch|first7=H.|title=High structural order in thin films of the organic semiconductor diindenoperylene|journal=Applied Physics Letters|volume=81|pages=2276|year=2002|doi=10.1063/1.1508436|issue=12|bibcode = 2002ApPhL..81.2276D }}</ref> and its ] temperature is above 330 °C.<ref>A. C. Dürr, Ph.D. thesis, Universität Stuttgart (2002)</ref> It is non-polar and therefore only slightly ], for example in ]. |
|
|
|
|
|
DIP is a red ]<ref>{{cite journal|last1=Heilig|first1=M|last2=Domhan|first2=M|last3=Port|first3=H|title=Optical properties and morphology of thin diindenoperylene films|journal=Journal of Luminescence|volume=110|pages=290|year=2004|doi=10.1016/j.jlumin.2004.08.023}}</ref> and has been used as active material for ].<ref>H. E. Simmons. (1987)</ref> Because of its ‘perylene-type’ optical emission in the visible spectrum, it has also been used in ]s.<ref>H. Antoniadis, A. J. Bard. (Hewlett-Packard Company & The Board of Regents of The University of Palo Alto, CA, 1997)</ref> Organic ]s of DIP have been studied.<ref>M. Münch, Ph.D. thesis, Universität Stuttgart (2001)</ref> The ] achieved was up to 0.1 cm²/(V·s) for thin film ]s with ] as ], making DIP a good candidate for further optimisation.<ref>N. Karl, in R. Farchioni, G. Grosso, Eds. (Springer, Berlin, 2001), vol. II, ISBN 3540667210 pp. 283 ff.</ref> |
|
DIP is a red ]<ref>{{cite journal|last1=Heilig|first1=M|last2=Domhan|first2=M|last3=Port|first3=H|title=Optical properties and morphology of thin diindenoperylene films|journal=]|volume=110|pages=290|year=2004|doi=10.1016/j.jlumin.2004.08.023|issue=4|bibcode = 2004JLum..110..290H }}</ref> and has been used as active material for ].<ref>H. E. Simmons. (1987)</ref> Because of its ‘perylene-type’ optical emission in the visible spectrum, it has also been used in ]s.<ref>H. Antoniadis, A. J. Bard. (Hewlett-Packard Company & The Board of Regents of The University of Palo Alto, CA, 1997)</ref> Organic ]s of DIP have been studied.<ref>M. Münch, Ph.D. thesis, Universität Stuttgart (2001)</ref> The ] achieved was up to 0.1 cm<sup>2</sup>/(V·s) for thin film ]s with ] as ], making DIP a good candidate for further optimisation.<ref>N. Karl, in R. Farchioni, G. Grosso, Eds. (Springer, Berlin, 2001), vol. II, {{ISBN|3-540-66721-0}} pp. 283 ff.</ref> |
|
|
|
|
|
The structure of bulk DIP ]s has recently been studied by Pflaum et al., who found two distinct phases at room temperature and at temperatures above 160 °C. In thin films for growth ‘near equilibrium’ (at substrate temperature of about 130 °C) by organic molecular beam deposition (OMBD), DIP has been shown to order very well.<ref name=clar/><ref name=Kowarik/> The structure of thin DIP films has been characterized ‘post-growth’,<ref name=clar/><ref>{{cite journal|last1=Dürr|first1=A.|last2=Schreiber|first2=F.|last3=Ritley|first3=K.|last4=Kruppa|first4=V.|last5=Krug|first5=J.|last6=Dosch|first6=H.|last7=Struth|first7=B.|title=Rapid Roughening in Thin Film Growth of an Organic Semiconductor (Diindenoperylene)|journal=Physical Review Letters|volume=90|pages=016104|year=2003|doi=10.1103/PhysRevLett.90.016104|bibcode=2003PhRvL..90a6104D}}</ref><ref>{{cite journal|last1=Dürr|first1=A.|last2=Koch|first2=N.|last3=Kelsch|first3=M.|last4=Rühm|first4=A.|last5=Ghijsen|first5=J.|last6=Johnson|first6=R.|last7=Pireaux|first7=J.-J.|last8=Schwartz|first8=J.|last9=Schreiber|first9=F.|title=Interplay between morphology, structure, and electronic properties at diindenoperylene-gold interfaces|journal=Physical Review B|volume=68|pages=115428|year=2003|doi=10.1103/PhysRevB.68.115428}}</ref><ref>{{cite journal|last1=Hoshino|first1=A|title=Epitaxial growth of organic crystals on organic substrates — polynuclear aromatic hydrocarbons|journal=Journal of Crystal Growth|volume=115|pages=826|year=1991|doi=10.1016/0022-0248(91)90854-X}}</ref> with structures differing from the room-temperature bulk structure. These thin-film structures depend on the substrate used, and also on the substrate temperature during growth.<ref name=Kowarik>{{cite journal|last1=Kowarik|first1=S.|last2=Gerlach|first2=A.|last3=Sellner|first3=S.|last4=Schreiber|first4=F.|last5=Cavalcanti|first5=L.|last6=Konovalov|first6=O.|title=Real-Time Observation of Structural and Orientational Transitions during Growth of Organic Thin Films|journal=Physical Review Letters|volume=96|pages=125504|year=2006|doi=10.1103/PhysRevLett.96.125504|bibcode=2006PhRvL..96l5504K}}</ref> |
|
The structure of bulk DIP ]s has recently been studied by Pflaum et al., who found two distinct phases at room temperature and at temperatures above 160 °C. In thin films for growth ‘near equilibrium’ (at substrate temperature of about 130 °C) by organic molecular beam deposition (OMBD), DIP has been shown to order very well.<ref name=clar/><ref name=Kowarik/> The structure of thin DIP films has been characterized ‘post-growth’,<ref name=clar/><ref>{{cite journal|last1=Dürr|first1=A.|last2=Schreiber|first2=F.|last3=Ritley|first3=K.|last4=Kruppa|first4=V.|last5=Krug|first5=J.|last6=Dosch|first6=H.|last7=Struth|first7=B.|title=Rapid Roughening in Thin Film Growth of an Organic Semiconductor (Diindenoperylene)|journal=Physical Review Letters|volume=90|pages=016104|year=2003|doi=10.1103/PhysRevLett.90.016104|bibcode=2003PhRvL..90a6104D|pmid=12570630|issue=1}}</ref><ref>{{cite journal|last1=Dürr|first1=A.|last2=Koch|first2=N.|last3=Kelsch|first3=M.|last4=Rühm|first4=A.|last5=Ghijsen|first5=J.|last6=Johnson|first6=R.|last7=Pireaux|first7=J.-J.|last8=Schwartz|first8=J.|last9=Schreiber|first9=F.|title=Interplay between morphology, structure, and electronic properties at diindenoperylene-gold interfaces|journal=Physical Review B|volume=68|pages=115428|year=2003|doi=10.1103/PhysRevB.68.115428|issue=11|bibcode = 2003PhRvB..68k5428D |display-authors=9|last10=Dosch|first10=H.|last11=Kahn|first11=A.|url=http://bib-pubdb1.desy.de/search?p=id:%22PUBDB-2017-11185%22}}</ref><ref>{{cite journal|last1=Hoshino|first1=A|title=Epitaxial growth of organic crystals on organic substrates — polynuclear aromatic hydrocarbons|journal=Journal of Crystal Growth|volume=115|issue=1–4|pages=826–830|year=1991|doi=10.1016/0022-0248(91)90854-X|bibcode = 1991JCrGr.115..826H |last2=Isoda|first2=Seiji|last3=Kobayashi|first3=Takashi}}</ref> with structures differing from the room-temperature bulk structure. These thin-film structures depend on the substrate used, and also on the substrate temperature during growth.<ref name=Kowarik>{{cite journal|last1=Kowarik|first1=S.|last2=Gerlach|first2=A.|last3=Sellner|first3=S.|last4=Schreiber|first4=F.|last5=Cavalcanti|first5=L.|last6=Konovalov|first6=O.|s2cid=1223144|title=Real-Time Observation of Structural and Orientational Transitions during Growth of Organic Thin Films|journal=Physical Review Letters|volume=96|pages=125504|year=2006|doi=10.1103/PhysRevLett.96.125504|bibcode=2006PhRvL..96l5504K|issue=12|pmid=16605925}}</ref> |
|
|
|
|
|
==References== |
|
==References== |
| Line 41: |
Line 59: |
|
] |
|
] |
|
] |
|
] |
|
|
|
|
] |
|