Related Experiment Video
Updated: Apr 12, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Triplet energies and excimer formation in meta- and para-linked carbazolebiphenyl matrix materials
Sergey A Bagnich1, Alexander Rudnick1, Pamela Schroegel2
1Experimental Physics II, Department of Physics, University of Bayreuth, 95440 Bayreuth, Germany Bayreuth Institute of Macromolecular Research (BIMF), University of Bayreuth, 95440 Bayreuth, Germany.
Abstract:
We present a spectroscopic investigation on the effect of changing the position where carbazole is attached to biphenyl in carbazolebiphenyl (CBP) on the triplet state energies and the propensity to excimer formation. For this, two CBP derivatives have been prepared with the carbazole moieties attached at the (para) 4- and 4(')-positions (pCBP) and at the (meta) 3- and 3(')-positions (mCBP) of the biphenyls. These compounds are compared to analogous mCDBP and pCDBP, i.e. two highly twisted carbazoledimethylbiphenyls, which have a high triplet energy at about 3.0 eV and tend to form triplet excimers in a neat film. This torsion in the structure is associated with localization of the excited state onto the carbazole moieties. We find that in mCBP and pCBP, excimer formation is prevented by localization of the triplet excited state onto the central moiety. As conjugation can continue from the central biphenyls into the nitrogen of the carbazole in the para-connected pCBP, emission involves mainly the benzidine. By contrast, the meta-linkage in mCBP limits conjugation to the central biphenyl. The associated shorter conjugation length is the reason for the higher triplet energy of 2.8 eV in mCBP compared with the 2.65 eV in pCBP.
Related Concept Videos
π Molecular Orbitals of 1,3-Butadiene
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
Hybridization of Atomic Orbitals II
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Radicals: Electronic Structure and Geometry
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
Structure of Benzene: Molecular Orbital Model

