NDLI: X-ray diffraction, DFT, and spectroscopic study of N,N′-difluoroboryl-5-(2-thienyl)dipyrrin and fluorescence studies of related dipyrromethanes, dipyrrins and BF$_{2}$-dipyrrins and DFT conformational study of 5-(2-thienyl)dipyrrin

Content Provider	Springer Nature Link
Author	Choi, Shin Hei Kim, Kibong Lee, Junseong Do, Youngkyu Churchill, David G.
Copyright Year	2007
Abstract	To explore the characteristics of potential fluorescent probes that could be used to screen prospective HDS catalysts, new 5-thienyl dipyrromethene derivatives have been prepared. 5-(2-thienyl)- (1a), 5-(3-thienyl)- (1b), and 5-(3-(2,5-dibromothienyl))-dipyrromethane (1c), were oxidized with DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) separately to give the corresponding dipyrrins 2a–2c. These were subsequently treated with F$_{3}$B·OEt$_{2}$ to afford the respective N,N′-difluoroboryl-5-(thienyl)dipyrrin compounds, 3a–3c; the latter two may serve as polymer precursors. Significant fluorescence signal enhancement is achieved with 3a–3c over 2a–2c. Orange fluorescence is observed for 3a whereas its isomer 3b gives green fluorescence (365 nm). An X-ray diffraction study of 3a was performed (orthorhombic, P2$_{1}$2$_{1}$2$_{1}$, a=10.684(10) Å, b=15.208(13) Å, c=7.256(6) Å, V=1179.0(17) Å$^{3}$, Z=4, R $_{1}$=0.0428, wR $_{2}$=0.0686) and its geometry was studied by way of DFT (Gaussian 03; B3LYP/6-31G$^{*}$) to give a HOMO/LUMO energy level difference of 414 nm, and a 2-thienyl group rotational barrier of ∼6 kcal/mol, compared to that of ∼12 kcal/mol for the phenyl derivative. Theoretical modeling of 2a demonstrated that the [N–H⋯N] interaction is favored by ca. 10 kcal/mol, whereas [N–H⋯S] bonding is sterically unattainable.
Starting Page	315
Ending Page	331
Page Count	17
File Format	PDF
ISSN	10741542
Journal	Journal of Chemical Crystallography
Volume Number	37
Issue Number	5
e-ISSN	15728854
Language	English
Publisher	Kluwer Academic Publishers-Plenum Publishers
Publisher Date	2007-03-06
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Inorganic Chemistry Physical Chemistry Crystallography Organometallic Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics

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