1,2,3‐Tri(9‐anthryl)benzene: Photophysical Properties and Solid State Intermolecular Interactions of Radially Arranged, Congested Aromatic π‐Planes

ABSTRACTThe optical properties of substituted and unsubstituted oligothiophenes are analysed with respect to their supramolecular organization in the solid state. The spectra typical of the isolated molecules are obtained by reducing the intermolecular interactions by both lateral chain substitution and by inclusion in a host organic crystal. The photophysical properties of the weakly interacting oligothiophenes are strongly influenced by their backbone conformation and conformational mobility. Oligomers included in the channels of a guest crystal show fast torsional relaxation processes during the photoexcitation. Powders of β-substituted oligomers display optical properties dependent on the conformation of their particular chain packing arrangement.

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Synthesis of a New Series of Organic Solid-State Near-Infrared Emitters: The Role of Crystal Packing and Weak Intermolecular Interactions and Application in Latent Fingerprint Detection

Crystal Growth & Design ◽

10.1021/acs.cgd.0c01392 ◽

2021 ◽

Vol 21 (2) ◽

pp. 1062-1076

Author(s):

Ranjit Singh ◽

Abhishek Kumar Gupta ◽

Chullikkattil P. Pradeep

Keyword(s):

Solid State ◽

Intermolecular Interactions ◽

Near Infrared ◽

Crystal Packing ◽

Latent Fingerprint ◽

Weak Intermolecular Interactions ◽

Organic Solid ◽

Infrared Emitters ◽

Fingerprint Detection

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Convenient Access to Functionalized Non-Symmetrical Atropisomeric 4,4′-Bipyridines

Compounds ◽

10.3390/compounds1020006 ◽

2021 ◽

Vol 1 (2) ◽

pp. 58-74

Author(s):

Emmanuel Aubert ◽

Emmanuel Wenger ◽

Paola Peluso ◽

Victor Mamane

Keyword(s):

Solid State ◽

Intermolecular Interactions ◽

Medicinal Chemistry ◽

Crystal Packing ◽

Cross Coupling ◽

Coupling Reactions ◽

Halogen Bonds ◽

Cross Coupling Reactions ◽

Cyano Groups ◽

Post Functionalization

Non-symmetrical chiral 4,4′-bipyridines have recently found interest in organocatalysis and medicinal chemistry. In this regard, the development of efficient methods for their synthesis is highly desirable. Herein, a series of non-symmetrical atropisomeric polyhalogenated 4,4′-bipyridines were prepared and further functionalized by using cross-coupling reactions. The desymmetrization step is based on the N-oxidation of one of the two pyridine rings of the 4,4′-bipyridine skeleton. The main advantage of this methodology is the possible post-functionalization of the pyridine N-oxide, allowing selective introduction of chlorine, bromine or cyano groups in 2- and 2′-postions of the chiral atropisomeric 4,4′-bipyridines. The crystal packing in the solid state of some newly prepared derivatives was analyzed and revealed the importance of halogen bonds in intermolecular interactions.

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Water-Soluble Pyrene-Adorned Imidazolium Salts with Multicolor Solid-State Fluorescence: Synthesis, Structure, Photophysical Properties, and Application on the Detection of Latent Fingerprints

ACS Omega ◽

10.1021/acsomega.1c00679 ◽

2021 ◽

Author(s):

Muthukumaran Nirmala ◽

Ramanan Vadivel ◽

Selvaraju Chellappan ◽

Jan Grzegorz Malecki ◽

Perumal Ramamurthy

Keyword(s):

Solid State ◽

Photophysical Properties ◽

Water Soluble ◽

Imidazolium Salts ◽

Latent Fingerprints ◽

Solid State Fluorescence

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Fluorinated azobenzenes as supramolecular halogen-bonding building blocks

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.15.197 ◽

2019 ◽

Vol 15 ◽

pp. 2013-2019 ◽

Cited By ~ 1

Author(s):

Esther Nieland ◽

Oliver Weingart ◽

Bernd M Schmidt

Keyword(s):

Solid State ◽

Dft Calculations ◽

Visible Light ◽

Half Life ◽

Photophysical Properties ◽

Bathochromic Shift ◽

Halogen Bonding ◽

Building Blocks ◽

Partial Overlap

ortho-Fluoroazobenzenes are a remarkable example of bistable photoswitches, addressable by visible light. Symmetrical, highly fluorinated azobenzenes bearing an iodine substituent in para-position were shown to be suitable supramolecular building blocks both in solution and in the solid state in combination with neutral halogen bonding acceptors, such as lutidines. Therefore, we investigate the photochemistry of a series of azobenzene photoswitches. Upon introduction of iodoethynyl groups, the halogen bonding donor properties are significantly strengthened in solution. However, the bathochromic shift of the π→π* band leads to a partial overlap with the n→π* band, making it slightly more difficult to address. The introduction of iodine substituents is furthermore accompanied with a diminishing thermal half-life. A series of three azobenzenes with different halogen bonding donor properties are discussed in relation to their changing photophysical properties, rationalized by DFT calculations.

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Indenopyrans – synthesis and photoluminescence properties

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.12.81 ◽

2016 ◽

Vol 12 ◽

pp. 825-834 ◽

Cited By ~ 2

Author(s):

Andreea Petronela Diac ◽

Ana-Maria Ţepeş ◽

Albert Soran ◽

Ion Grosu ◽

Anamaria Terec ◽

...

Keyword(s):

Solid State ◽

Emission Band ◽

Fluorescence Spectra ◽

Photophysical Properties ◽

Quantum Yields ◽

Band Broadening ◽

Photoluminescence Properties ◽

Fluorescence Quantum Yields ◽

Blue Emitters ◽

Solid State Fluorescence

New indeno[1,2-c]pyran-3-ones bearing different substituents at the pyran moiety were synthesized and their photophysical properties were investigated. In solution all compounds were found to be blue emitters and the trans isomers exhibited significantly higher fluorescence quantum yields (relative to 9,10-diphenylanthracene) as compared to the corresponding cis isomers. The solid-state fluorescence spectra revealed an important red shift of λmax due to intermolecular interactions in the lattice, along with an emission-band broadening, as compared to the solution fluorescence spectra.

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