The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Dyes Modified for Extended Conjugation and Restricted Bond Rotations
Abstract
Five new, constrained, aryl-substituted 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BODIPY) dyes (3f,g and 4h-j) were prepared and investigated to see if they have more favorable fluorescence characteristics than the unconstrained systems 2 that were prepared in previous studies. Dye types 3 and 4 have relatively rigid conformations caused by the heteroatom (3f and 3g) or ethylene bridge (4h-j) linkers that preclude free rotation of the substituted-benzene molecular fragments. In the event, the new dye types 3 and 4 have longer lambda(max abs) (620-660 nm) and lambda(max)(fluor) (630-680 nm) values than compounds 2. They also exhibit higher extinction coefficients (>100 000 M(-1) cm(-1), except for 3g). Their fluorescent quantum yields are high (up to 0.72 for 4j), with the exception of compound 3g, which has a quantum yield of only 0.05. The redox properties of dyes 3 and 4 have also been examined.
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Cites
van der Waals Volumes and Radii
Bondi, A. (1964) · The Journal of Physical Chemistry · doi:10.1021/j100785a001 · Cited by 19,350
Burghart, A., Kim, H., Welch, M. B., Thoresen, L. H., Reibenspies, J., Burgess, K., Bergström, F., & Johansson, L. B.-Å. (1999) · The Journal of Organic Chemistry · doi:10.1021/jo990796o · Cited by 369
Self-citationLavigne, J. J., Savoy, S., Clevenger, M. B., Ritchie, J. E., McDoniel, B., Yoo, S.-J., Anslyn, E. V., McDevitt, J. T., Shear, J. B., & Neikirk, D. (1998) · Journal of the American Chemical Society · doi:10.1021/ja9743405 · Cited by 230
Cited by
BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties
Loudet, A., & Burgess, K. (2007) · Chemical Reviews · doi:10.1021/cr078381n · Cited by 5,238
Self-citationThe Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed
Ulrich, G., Ziessel, R., & Harriman, A. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200702070 · Cited by 3,161
Recent Strategies to Develop Innovative Photosensitizers for Enhanced Photodynamic Therapy
Pham, T. C., Nguyen, V.-N., Choi, Y., Lee, S., & Yoon, J. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00381 · Cited by 1,813
The Chemistry of β-Diketiminatometal Complexes
Bourget-Merle, L., Lappert, M. F., & Severn, J. R. (2002) · Chemical Reviews · doi:10.1021/cr010424r · Cited by 1,049
Near‐Infrared Organic Compounds and Emerging Applications
Qian, G., & Wang, Z. Y. (2010) · Chemistry – An Asian Journal · doi:10.1002/asia.200900596 · Cited by 772
Metadata
- Authors
- Chen, J., Burghart, A., Derecskei-Kovacs, A., & Burgess, K.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-04-18
- Volume
- 65
- Issue
- 10
- Pages
- 2900-2906
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2082273137
- Cited by
- 278
- References
- 3
- FWCI
- 4.25
- Type
- journal article
- Language
- en
- Open access
- closed
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